Nitrogen-containing heterocycles

ABSTRACT

Optically active nitrogen-containing heterocycles of the formula I according to claim 1 are suitable as components for ferroelectric liquid crystalline materials.

This is a division of Ser. No. 07/352,308, filed May 16, 1989, now U.S.Pat. No. 5,089,168, which is a division of Ser. No. 07/034,182, filedDec. 24, 1986, now U.S. Pat. No. 4,834,904, which is based on PCT/EP86/00248 of Apr. 23, 1986.

The invention relates to nitrogen-containing heterocycles of the formulaI

    R.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --R.sup.2            I

in which

one of the radicals R¹ and R² is H, an unsubstituted or substitutedalkyl group of 1-15 carbon atoms in which one or two non-adjacent CH₂groups can also be replaced by at least one member of the group --O--,--CO--, --O--CO--, --CO--O-- and --CH═CH--; F, Cl, Br, --CN, --NCS or R³--(A³)_(p) --Z² --,

the other radical R¹ or R² is an optically active organic radical withan asymmetric carbon atom,

A¹ is --A--, --A⁴ --Z³ --A-- or --A--Z³ --A⁴ --,

A is a 1,4-phenylene group in which at least one CH group is replaced byN,

A², A³ and A⁴ each are 1,4-phenylene which is unsubstituted orsubstituted by one or two F atoms and/or Cl atoms and/or CH₃ groupsand/or CN groups, in which one or two CH groups can also be replaced byN atoms; 1,4-cyclohexylene in which one or two non-adjacent CH₂ groupscan also be replaced by O atoms and/or S atoms; piperidine-1,4-diyl,1,4-bicyclo(2,2,2)octylene; decahydronaphthalene-2,6-diyl which isunsubstituted or substituted by CN; or1,2,3,4-tetrahydronaphthalene-2,6-diyl,

Z¹, Z² and Z³ each are --CO--O, --O--CO--, --OCH₂ --, --CH₂ O--, --CH₂CH₂ --, substituted ethylene or a single bond,

R³ is H; an unsubstituted or substituted alkyl group of 1-15 carbonatoms in which one or two non-adjacent CH₂ groups can also be replacedby a member of the group --O--, --CO--, --O--CO--, --CO--O and--CH═CH--; F, Cl, Br, --NCS or --CN, and

p is 1 or 2,

in which the groups A³ can be the same or can differ from each other,when p=2, with the proviso that when A=pyrimidine-2,5-diyl, one of theradicals R¹ and R² is an optically active organic radical and the otherradical R¹ or R² is an unsubstituted or substituted alkyl group of 1-15carbon atoms, in which one or two non-adjacent CH₂ groups can also bereplaced by at least one member of the group --O--, --CO--, --O--CO--,--CO--O-- and --CH═CH--.

For the sake of simplicity, in the following text Cy is a1,4-cyclohexylene group, Dio is a 1,3-dioxane-2,5-diyl group, Dit is a1,3-dithiane-2,5-diyl group, Bi is a 1,4-bicyclo(2,2,2)octylene group,Phe is a 1,4-phenylene group and Pyr is a 1,4-phenylene group in whichat least one CH group is replaced by N, in which these groups, inparticular Cy and Phe can be unsubstituted or substituted by one or twoF and/or Cl atoms and/or CH₃ groups and/or CN groups.

Similar compounds are known from, for example, EP-OS 0 131 373. However,in contrast to the above, the compounds disclosed therein do not containnitrogen-containing heterocyclic rings.

The compounds of the formula I can be used, like similar compounds, aschiral dopants for liquid crystalline phases, in particular ascomponents of ferroelectric liquid crystalline phases. These phases aresuitable for displays, which are based on the principle of the twistedcell (IN displays), the guest-host effect, the effect of the deformationof aligned phases or the effect of dynamic scattering, in particular,however, for ferroelectric displays, for example in accordance with N.A. Clark and S. T. Lagerwall, Applied Phys. Lett. 36, 899 (1980).

The invention was based on the object of finding new stable liquidcrystalline or mesogenic compounds that would be suitable as componentsof such phases.

It has been found that the compounds of the formula I are highlysuitable as components of liquid crystalline phases. In particular, theycan be used for preparing stable chiral S_(c) phases in a temperaturerange favourable for electrooptical applications.

On adding compounds of the formula I to non-polar liquid crystallinephases, it was found, surprisingly, that even relatively small additionscan significantly increase spontaneous polarization.

In addition, by providing the compounds of the formula I the range ofliquid crystalline substances that are suitable for the preparation offerroelectric mixtures from various points of view relating toapplication, has in general been substantially broadened.

The compounds of the formula I have a wide range of applications.Depending on the choice of substituents, these compounds can serve asbase materials which form the predominant part of liquid crystallinephases; however, compounds of the formula I can be treated with liquidcrystalline base materials from other compound classes in order to vary,for example, the dielectric and/or optical anisotropy and/or thespontaneous polarization of such a phase. Furthermore, the compounds ofthe formula I are suitable as intermediate products for the preparationof other substances that can be utilized as components of liquidcrystalline phases.

When pure, the compounds of the formula I are colourless and form liquidcrystalline mesophases in a temperature range favourable forelectro-optical applications. They are very stable against the action ofchemicals, heat and light.

The invention thus relates to the compounds of the formula I as well asto the use of the compounds of the formula I as components of liquidcrystalline phases. In addition, the invention relates to liquidcrystalline phases, in particular ferro-electric liquid crystallinephases, containing at least one compound of the formula I as well asliquid crystal display elements, in particular electro-optical displayelements, comprising such phases.

In the preceding and in the following, R¹, R², R³, A, A¹, A², A³, A⁴,Z¹, Z², Z³ and p have the meaning given, unless expressly indicatedotherwise.

Accordingly, the compounds of the formula I comprise in particularcompounds of the partial formulae I1 and I2 (with two rings),I3-I20(with 3 rings), I21-I71 (with 4 rings), as well as I72-I94 (with 5rings):

    R.sup.1 --A--A.sup.2 --R.sup.2                             I 1

    R.sup.1 --A--Z.sup.1 --A.sup.2--R.sup.2                    I 2

    R.sup.1 --A.sup.4 --A--A.sup.2 --R.sup.2                   I 3

    R.sup.1 --A--A.sup.4 --A.sup.2 --R.sup.2                   I 4

    R.sup.3 --A.sup.3 --A--A.sup.2 --R.sup.2                   I 5

    R.sup.1 --A--A.sup.2 --A.sup.3 --R.sup.3                   I 6

    R.sup.1 --A.sup.4 --Z.sup.3 --A--A.sup.2 --R.sup.2         I 7

    R.sup.1 --A--Z.sup.3 --A.sup.4 --A.sup.2 --R.sup.2         I 8

    R.sup.1 --A--Z.sup.1 --A.sup.2 --A.sup.3 --R.sup.3         I 9

    R.sup.1 --A.sup.4 --Z.sup.3 --A--A.sup.2 --R.sup.2         I 10

    R.sup.1 --A--Z.sup.3 --A.sup.4 --A.sup.2 --R.sup.2         I 11

    R.sup.1 --A.sup.4 --A--Z.sup.1 --A.sup.2 --R.sup.2         I 12

    R.sup.1 --A--A.sup.4 --Z.sup.1 --A.sup.2 --R.sup.2         I 13

    R.sup.3 --A.sup.3 --A--Z.sup.1 --A.sup.2 --R.sup.2         I 14

    R.sup.1 --A--A.sup.2 --Z.sup.2 --A.sup.3 --R.sup.3         I 15

    R.sup.3 --A.sup.3 --Z.sup.2 --A--A.sup.2 --R.sup.2         I 16

    R.sup.3 --A.sup.3 --Z.sup.2 --A--Z.sup.1 --A.sup.2 --R.sup.2I 17

    R.sup.1 --A--Z.sup.1 --A.sup.2 --Z.sup.2 --A.sup.3 --R.sup.3I 18

    R.sup.1 --A.sup.4 --Z.sup.3 --A--Z.sup.1 --A.sup.2 --R.sup.2I 19

    R.sup.1 --A--Z.sup.3 --A.sup.4 --Z.sup.1 --A.sup.2 --R.sup.2I 20

    R.sup.3 --A.sup.3 --A.sup.4 --A--A.sup.2 --R.sup.2         I 21

    R.sup.3 --A.sup.3 --A--A.sup.4 --A.sup.2 --R.sup.2         I 22

    R.sup.1 --A.sup.4 --A--A.sup.2 --A.sup.3 --R.sup.3         I 23

    R.sup.1 --A--A.sup.4 --A.sup.2 --A.sup.3 --R.sup.3         I 24

    R.sup.3 --A.sup.3 --A--A.sup.2 --A.sup.3 --R.sup.3         I 25

    R.sup.3 --A.sup.3 --A.sup.3 --A--A.sup.2 --R.sup.3         I 26

    R.sup.1 --A--A.sup.2 --A.sup.3 --A.sup.3 --R.sup.3         I 27

    R.sup.3 --A.sup.3 --Z.sup.2 --A--A.sup.2 --A.sup.3 --R.sup.3I 28

    R.sup.3 --A.sup.3 --A--Z.sup.1 --A.sup.2 --A.sup.3 --R.sup.3I 29

    R.sup.3 --A.sup.3 --A--Z.sup.1 --A.sup.2 --A.sup.3 --R.sup.3I 30

    R.sup.3 --A.sup.3 --A--A.sup.2 --Z.sup.2 --A.sup.3 --R.sup.3I 31

    R.sup.1 --A--A.sup.4 --Z.sup.1 --A.sup.2 --A.sup.3 --R.sup.3I 32

    R.sup.1 --A.sup.4 --A--Z.sup.1 --A.sup.2 --A.sup.3 --R.sup.3I 33

    R.sup.3 --A.sup.3 --A.sup.4 --A--Z.sup.1 --A.sup.2 --R.sup.2I 34

    R.sup.3 --A.sup.3 --A--A.sup.4 --Z.sup.1 --A.sup.2 --R.sup.2I 35

    R.sup.1 --A.sup.4 --A--A.sup.2 --Z.sup.2 --A.sup.3 --R.sup.3I 36

    R.sup.1 --A--A.sup.4 --A.sup.2 --Z.sup.2 --A.sup.3 --R.sup.3I 37

    R.sup.3 --A.sup.3 --Z.sup.2 --A.sup.4 --A--A.sup.2 --R.sup.2I 38

    R.sup.3 --A.sup.3 --Z.sup.2 --A--A.sup.4 --A.sup.2 --R.sup.2I 39

    R.sup.3 --A.sup.3 --A--A.sup.2 --Z.sup.2 --A.sup.3 --R.sup.3I 40

    R.sup.3 --A.sup.3 --Z.sup.2 --A--A.sup.2 --A.sup.3 --R.sup.3I 41

    R.sup.3 --A.sup.3 --A.sup.3 --A--Z.sup.1 --A.sup.2 --R.sup.2I 42

    R.sup.3 --A.sup.3 --A.sup.4 --Z.sup.3 --A--A.sup.2 --R.sup.2I 43

    R.sup.3 --A.sup.3 --A--Z.sup.3 --A.sup.4 --A.sup.2 --R.sup.2I 44

    R.sup.1 --A--A.sup.2 --Z.sup.2 --A.sup.3 --A.sup.3 --R.sup.3I 45

    R.sup.1 --A.sup.4 --Z.sup.3 --A--A.sup.2 --A.sup.3 --R.sup.3I 46

    R.sup.1 --A--Z.sup.3 --A.sup.4 --A.sup.2 --A.sup.3 --R.sup.3I 47

    R.sup.3 --A.sup.3 --A.sup.3 --Z.sup.2 --A--A.sup.2 --R.sup.2I 48

    R.sup.1 --A--Z.sup.1 --A.sup.2 --A.sup.3 --A.sup.3 --R.sup.3I 49

    R.sup.3 --A.sup.3 --Z.sup.2 --A.sup.4 --A--Z.sup.1 --A.sup.2 --R.sup.2I 50

    R.sup.3 --A.sup.3 --Z.sup.2 --A--A.sup.4 --Z.sup.1 --A.sup.2 --R.sup.2I 51

    R.sup.1 --A.sup.4 --A--Z.sup.1 --A.sup.2 --Z.sup.2 --A.sup.3 --R.sup.3I 52

    R.sup.1 --A--A.sup.4 --Z.sup.1 --A.sup.2 --Z.sup.2 --A.sup.3 --R.sup.3I 53

    R.sup.3 --A.sup.3 --A--Z.sup.1 --A.sup.2 --Z.sup.2 --A.sup.3 --R.sup.3I 54

    R.sup.3 --A.sup.3 --Z.sup.2 --A--A.sup.2 --Z.sup.2 --A.sup.3 --R.sup.3I 55

    R.sup.3 --A.sup.3 --Z.sup.2 --A--Z.sup.1 --A.sup.2 --A.sup.3 --R.sup.2I 56

    R.sup.3 --A.sup.3 --A.sup.4 --Z.sup.3 --A--Z.sup.1 --A.sup.2 --R.sup.2I 57

    R.sup.3 --A.sup.3 --A--Z.sup.3 --A.sup.4 --Z.sup.1 --A.sup.2 --R.sup.2I 58

    R.sup.1 --A.sup.4 --Z.sup.3 --A--A.sup.2 --Z.sup.2 --A.sup.3 --R.sup.3I 59

    R.sup.1 --A--Z.sup.3 --A.sup.4 --A.sup.2 --Z.sup.2 --A.sup.3 --R.sup.3I 60

    R.sup.3 --A.sup.3 --Z.sup.2 --A.sup.4 --Z.sup.3 --A--A.sup.2 --R.sup.2I 61

    R.sup.3 --A.sup.3 --Z.sup.2 --A--Z.sup.3 --A.sup.4 --A.sup.2 --R.sup.2I 62

    R.sup.1 --A.sup.4 --Z.sup.3 --A--Z.sup.1 --A.sup.2 --A.sup.3 --R.sup.3I 63

    R.sup.1 --A--Z.sup.3 --A.sup.4 --Z.sup.1 --A.sup.2 --A.sup.3 --R.sup.3I 64

    R.sup.3 --A.sup.3 --A.sup.3 --Z.sup.2 --A--Z.sup.1 --A.sup.2 --R.sup.2I 65

    R.sup.1 --A--Z.sup.1 --A.sup.2 --Z.sup.2 --A.sup.3 --A.sup.3 --R.sup.3I 66

    R.sup.3 --A.sup.3 --Z.sup.2 --A--Z.sup.1 --A.sup.2 --Z.sup.2 --A.sup.3 --R.sup.3                                                 I 67

    R.sup.3 --A.sup.3 --Z.sup.2 --A.sup.4 --Z.sup.3 --A--Z.sup.1 --A.sup.2 --R.sup.2                                                 I 68

    R.sup.3 --A.sup.3 --Z.sup.2 --A--Z.sup.3 --A.sup.4 --Z.sup.1 --A.sup.2 --R.sup.2                                                 I 69

    R.sup.1 --A.sup.4 --Z.sup.3 --A--Z.sup.1 --A.sup.2 --Z.sup.2 --A.sup.3 --R.sup.3                                                 I 70

    R.sup.1 --A--Z.sup.3 --A.sup.4 --Z.sup.1 --A.sup.2 --Z.sup.2 --A.sup.3 --R.sup.3                                                 I 71

    R.sup.3 --A.sup.3 --A.sup.4 --A--A.sup.2 --A.sup.3 --R.sup.3I 72

    R.sup.3 --A.sup.3 --A--A.sup.4 --A.sup.2 --A.sup.3 --R.sup.3I 73

    R.sup.3 --A.sup.3 --A.sup.4 --A--A.sup.2 --A.sup.3 --R.sup.3I 73

    R.sup.3 --A.sup.3 --A--A.sup.4 --A.sup.2 --A.sup.3 --R.sup.3I 75

    R.sup.1 --A--A.sup.4 --A.sup.2 --A.sup.3 --A.sup.3 --R.sup.3I 76

    R.sup.3 --A.sup.3 --A.sup.4 --A--A.sup.2 --Z.sup.2 --A.sup.3 --R.sup.3I 77

    R.sup.3 --A.sup.3 --A--A.sup.4 --A.sup.2 --Z.sup.2 --A.sup.3 --R.sup.3I 78

    R.sup.3 --A.sup.3 --A.sup.4 --A--Z.sup.1 --A.sup.2 --A.sup.3 --R.sup.3I 79

    R.sup.3 --A.sup.3 --A--A.sup.4 --Z.sup.1 --A.sup.2 --A.sup.3 --R.sup.3I 80

    R.sup.3 --A.sup.3 --Z.sup.2 --A.sup.4 --A--A.sup.2 --A.sup.3 --R.sup.3I 81

    R.sup.3 --A.sup.3 --Z.sup.2 --A--A.sup.4 --A.sup.2 --A.sup.3 --R.sup.3I 82

    R.sup.3 --A.sup.3 --A.sup.4 --A--Z.sup.1 --A.sup.2 --Z.sup.2 --A.sup.3 --R.sup.3                                                 I 83

    R.sup.3 --A.sup.3 --A--A.sup.4 --Z.sup.1 --A.sup.2 --Z.sup.2 --A.sup.3 --R.sup.3                                                 I 84

    R.sup.3 --A.sup.3 --Z.sup.2 --A.sup.4 --A--A.sup.2 --Z.sup.2 --A.sup.3 --R.sup.3                                                 I 85

    R.sup.3 --A.sup.3 --Z.sup.2 --A--A.sup.4 --A.sup.2 --Z.sup.2 --A.sup.3 --R.sup.3                                                 I 86

    R.sup.3 --A.sup.3 --Z.sup.2 --A.sup.4 --A--Z.sup.1 --A.sup.2 --A.sup.3 --R.sup.3                                                 I 87

    R.sup.3 --A.sup.3 --Z.sup.2 --A--A.sup.4 --Z.sup.1 --A.sup.2 --A.sup.3 --R.sup.3                                                 I 88

    R.sup.3 --A.sup.3 --Z.sup.2 --A.sup.4 --A--Z.sup.1 --A.sup.2 --Z.sup.2 --A.sup.3 --R.sup.3                                       I 89

    R.sup.3 --A.sup.3 --Z.sup.2 --A--A.sup.4 --Z.sup.1 --A.sup.2 --Z.sup.2 --A.sup.3 --R.sup.3                                       I 90

    R.sup.1 --A.sup.4 --Z.sup.3 --A--Z.sup.1 --A.sup.2 --Z.sup.2 --A.sup.3 --A.sup.3 --R.sup.3                                       I 91

    R.sup.1 --A--Z.sup.3 --A.sup.4 --Z.sup.1 --A.sup.2 --Z.sup.2 --A.sup.3 --A.sup.3 --R.sup.3                                       I 92

    R.sup.3 --A.sup.3 --A.sup.3 --Z.sup.2 --A--Z.sup.1 --A.sup.2 --Z.sup.2 --A.sup.3 --R.sup.3                                       I 93

    R.sup.3 --A.sup.3 --Z.sup.2 --A--Z.sup.1 --A.sup.2 --Z.sup.2 --A.sup.3 --A.sup.3 --R.sup.3                                       I 94

Particularly preferred, relatively small groups of compounds are thoseof the formulae I001 to I022:

    R.sup.1 -Phe--Z.sup.1 --A--R.sup.2                         I 001

    R.sup.1 -Cy--Z.sup.1 --A--R.sup.2                          I 002

    R.sup.1 -Dio--Z.sup.1 --A--R.sup.2                         I 003

    R.sup.1 -Pip--Z.sup.1 --A--R.sup.2                         I 004

    R.sup.1 -Bi--Z.sup.1 --A--R.sup.2                          I 005

    R.sup.1 -Pyr--Z.sup.1 --A--R.sup.2                         I 006

    R.sup.1 -Phe--Z--A--Z.sup.2 --Phe--R.sup.2                 I 007

    R.sup.1 -Dio--Z.sup.1 --A--Z.sup.2 --Cy--R.sup.2           I 008

    R.sup.1 -Cy--Z.sup.1 --A--Z.sup.2 --Phe--R.sup.2           I 009

    R.sup.1 -Cy--Z.sup.1 --A--Z.sup.2 --Cy--R.sup.2            I 010

    R.sup.1 -Phe-Phe--Z.sup.1 --A--R.sup.2                     I 011

    R.sup.1 -Phe-Cy--Z.sup.1 --A--R.sup.2                      I 012

    R.sup.1 -Cy-Phe--Z.sup.1 --A--R.sup.2                      I 013

    R.sup.1 -Cy-Cy--Z.sup.1 --A--R.sup.2                       I 014

    R.sup.1 -Phe-Phe--Z.sup.1 --A--Z.sup.2 --Phe--R.sup.2      I 015

    R.sup.1 -Phe-Phe--Z.sup.1 --A--Z.sup.2 --Cy--R.sup.2       I 016

    R.sup.1 -Phe-Cy--Z.sup.1 --A--Z.sup.2 --Phe--R.sup.2       I 017

    R.sup.1 -Phe-Cy--Z.sup.1 --A--Z.sup.2 --Cy--R.sup.2        I 018

    R.sup.1 -Cy-Phe--Z.sup.1 --A--Z.sup.2 --Phe--R.sup.2       I 019

    R.sup.1 -Cy-Phe--Z.sup.1 --A--Z.sup.2 --Cy--R.sup.2        I 020

    R.sup.1 -Cy-Cy--Z.sup.1 --A--Z.sup.2 --Phe--R.sup.2        I 021

    R.sup.1 -Cy-Cy--Z.sup.1 --A--Z.sup.2 --Cy--R.sup.2         I 022

In the compounds of the above partial formulae I001 to I022, Z¹ and Z²are each, preferably, a single bond. The partial formulae I001, I009 andI013 are especially preferred.

In the compounds of the preceding and following formulae, a substitutedalkyl group or substituted ethylene represents an alkyl group or --CH₂CH₂ -- (ethylene) group which is monosubstituted or polysubstituted ondifferent carbon atoms by halogen, preferably fluorine or chlorine, orby CN. Preferably, the alkyl group is only monosubstituted by halogen orCN. The carbon atom linked to halogen or CN is preferably an asymmetriccarbon atom.

One of the radicals R¹ and R² is preferably, alkyl, --O--alkyl oroxaalkyl, --COO--alkyl, --OCO--alkyl, --CO--alkyl or alkenyl.

The alkenyl groups in the compounds of the formula I are preferablystraight-chain trans-alkenyl groups of the formula ##STR1## in which n2is 0 to 10, preferably 2 to 10, and n1 is 0 to 5, preferably 0.

The alkyl radicals in which one ("alkoxy" or "oxaalkyl") or two("alkoxyalkoxy" or "dioxaalkyl") non-adjacent CH₂ groups can be replacedby O atoms, can be straight-chain or branched. They are preferablystraight-chain, have 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15carbon atoms and therefore represent preferably 2-oxapropyl(═methoxymethyl), 2-(═ethoxymethyl) or 3-oxabutyl (═2-methoxymethyl),2-, 3- or 4-oxapentyl, 2-, 3-, 4- or 5-oxahexyl, 2-, 3-, 4-, 5- or6-oxaheptyl, 2-, 3-, 4-, 5-, 6- or 8-oxaoctyl, 2-, 3-, 4-, 5-, 6- or9-oxanonyl, 2-, 3-, 4-, 5-, 6- or 10-oxadecyl, 2-, 3-, 4-, 5-, 6- or 11-oxaundecyl, 2-, 3-, 4-, 5-, 6- or 12-oxadodecyl, 2-, 3-, 4-, 5-, 6- or13-oxatridecyl, 2-, 3-, 4-, 5-, 6- or 14-oxatetradecyl, 2-, 3-, 4-, 5-,6- or 15-oxapentadecyl, 1,3-dioxabutyl (═methoxymethoxy), 1,3-, 1,4- or2,4-dioxapentyl, 1,3-, 1,4-, 1,5-, 2,4-, 2,5- or 3,5-dioxahexyl, 1,3-,1,4-, 1,5-, 1,6-, 2,4-, 2,5-, 2,6-, 3,5-, 3,6- or 4,6-dioxaheptyl.

The alkyl radical in the groups R¹ and/or R² can be straight-chain orbranched. They are preferably straight-chain, possess 2, 3, 4, 5, 6, 7,8, 9, 10, 11 or 12, 13, 14 or 15 carbon atoms and are thereforepreferably ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl,decyl, undecyl, dodecyl, tridecyl, tetradecyl or pentadecyl, as well asmethyl.

The other radical R¹ or R² is an optically active organic radical withan asymmetric carbon atom. The asymmetric carbon atom is preferablylinked to two differently substituted carbon atoms, a hydrogen atom anda substituent selected from the group halogen (preferably F, Cl or Br),alkyl or alkoxy with 1 to 5 carbon atoms in each case, and CN. Theoptically active organic radical has preferably the formula ##STR2##wherein X is --CO--O--, --O--CO--, --O--CO--O--, --CO--, --O--, --S--,--CH═CH--, --CH═CH--COO-- or a single bond,

Q is alkylene with 1 to 5 carbon atoms, in which a CH₂ group not linkedwith X can also be replaced by --O--, --CO--, --O--CO--, --CO--O-- or--CH═CH--, or a single bond,

Y is CN, halogen, methyl or methoxy and

R is an alkyl group of 1 to 18 carbon atoms that is different from Y, inwhich one or two non-adjacent CH₂ groups can also be replaced by --O--,--CO--, --O--CO--, --CO--O-- and/or --CH═CH--.

X is preferably --CO--O--, --O--CO--, --O--, --CH═CH--COO-- (trans) or asingle bond. --O--, --CO--O-- and --O--CO-- are particularly preferred.

Q is preferably alkylene of 1 to 5 carbon atoms or a single bond, --CH₂--, --CH₂ CH₂ -- or a single bond being particularly preferred.

Y is preferably CH₃, --CN or Cl, --CN or Cl being particularlypreferred.

R is preferably straight-chain alkyl of 1 to 10, in particular of 1 to7, carbon atoms, in which, if desired, the CH₂ group linked to theasymmetric carbon atom can be replaced by --O--, --O--CO-- or --CO--O--.

R² in formula I is preferably the optically active radical.

A², A³ and A⁴ are preferably, independently of one another, Cy, Dio orPhe, furthermore, preferably, Dit, Pyr or Pip; the compound of theformula I does not contain, preferably, more than one of the radicalsDio, Dit, Pip, Bi, Pyn or Pyr.

A¹ is preferably --A-- or --A⁴ --Z³ --A--.

A is preferably pyrimidine-2,5-diyl, pyridine-2,5-diyl,pyridazine-3,6-diyl or pyrazine-2,5-diyl, pyrimidine-2,5-diyl orpyridine-2,5-diyl being particularly preferred.

Z¹, Z² and Z³ are preferably, independently of one another, --O--CO--,--CO--O-- groups or single bonds.

--A¹ --Z¹ --A² -- is preferably a structural element selected from thegroup of the formulae 1 to 4: ##STR3## Groups of the formulae 1 and 2are particularly preferred.

Among the compounds of the formula I as well as among the preceding andfollowing partial formulae, those are preferred in which at least one ofthe radicals contained therein possesses one of the given preferredmeanings. Relatively small groups of compounds which are particularlypreferred are those of the formulae I023 to I031:

    R°-Pyr-Phe-R*                                       I023

    R°-Pyr-Cy-R*                                        I024

    R°-Pyr--CH.sub.2 CH.sub.2 -Cy-R*                    I025

    R°-Pyr--COO--Phe-R*                                 I026

    R°-Pyr--OCO--Phe-R*                                 I027

    R°-Pyr--COO--Cy-R*                                  I028

    R°-Pyr-Phe--CH.sub.2 CH.sub.2 -Cy-R*                I029

    R°-Pyr-Phe--O--CH.sub.2 -Cy-R*                      I030

    R°-Pyr-Phe--O--CH.sub.2 -Phe-R*                     I031

in which R° is preferably straight-chain alkyl or alkoxy of, in eachcase, 2 to 12 carbon atoms, Pyr is preferably pyrimidine-2,5-diyl and R*preferably has one of the preferred meanings indicated for the opticallyactive organic radical.

Further relatively small groups of compounds which are preferred arethose of the formulae I032 to I096: ##STR4##

Other particularly preferred pyridine compounds are those of theformulae I097 to I117:

    R°-Pyr-Bi-R*                                        I097

    R°-Bi-Pyr-R*                                        I098

    R°-Pyr--OCO--Phe-R*                                 I099

    R°-Phe--COO--Pyr-R*                                 I100

    R°-Pyr-Phe-Cy-R*                                    I101

    R°-Cy-Phe-Pyr-R*                                    I102

    R°-Pyr-Phe-Phe-R*                                   I103

    R°-Phe-Phe-Pyr-R*                                   I104

    R°-Pyr-Phe-Bi-R*                                    I105

    R°-Bi-Phe-Pyr-R*                                    I106

    R°-Pyr-Bi-Phe-R*                                    I107

    R°-Phe-Bi-Pyr-R*                                    I108

    R°-Pyr-Cy-Cy-R*                                     I109

    R°-Cy-Cy-Pyr-R*                                     I110

    R°-Cy-Pyr-Cy-R*                                     I111

    R°-Pyr-Phe--CH.sub.2 CH.sub.2 --Cy-R*               I112

    R°-Cy--CH.sub.2 CH.sub.2 --Phe-Pyr-R*               I113

    R°-Pyr-Cy--CH.sub.2 CH.sub.2 --Cy-R*                I114

    R°-Cy--CH.sub.2 CH.sub.2 --Cy-Pyr-R*                I115

    R°-Phe-Pyr-Cy-R*                                    I116

    R°-Cy-Pyr-Phe-R*                                    I117

In the formulae I097 to I117, Pyr denotes pyridine-2,5-diyl.

Particularly preferred are optically active pyridine compounds of theformula I'

    R.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --R.sup.2            I

in which

one of the radicals R¹ and R² is H; an unsubstituted or substitutedalkyl group of 1-15 carbon atoms in which one or two non-adjacent CH₂groups can also be replaced by at least one member of the groups --O--,--CO--, --O--CO--, --CO--O-- and --CH═CH--; F, Cl, Br, --CN, --NCS or R³--(A³)_(p) --Z² --,

the other radical R¹ or R² is an optically active organic radical withan asymmetric carbon atom,

A¹ is --A--, --A⁴ --Z³ --A-- or --A--Z³ --A⁴ --,

A is 2,5-pyridinediyl,

A², A³ or A⁴ each are 1,4-phenylene which is unsubstituted orsubstituted by one or two F atoms and/or Cl atoms and/or CH₃ groupsand/or CN groups, in which one or two CH groups can also be replaced byN atoms; 1,4-cyclohexylene in which one or two non-adjacent CH₂ groupscan also be replaced by O atoms and/or S atoms; piperidine-1,4-diyl,1,4-bicyclo-(2,2,2)-octylene, decahydronaphthalene-2,6-diyl which isunsubstituted or substituted by CN; or1,2,3,4-tetrahydronaphthalene-2,6-diyl,

Z¹, Z² and Z³ each are --CO--O--, --O--CO--, --OCH₂ --, --CH₂ O--, --CH₂CH₂ --, substituted ethylene or a single bond,

R³ is H; an unsubstituted or substituted alkyl group of 1-15 carbonatoms in which one or two non-adjacent CH₂ groups can also be replacedby one member of the group --O--, --CO--, --O--CO--, --CO--O-- and--CH═CH--; F, Cl, Br, --NCS or --CN, and

p is 1 or 2,

in which the groups A³ can be the same or different from each other,when p=2, as well as liquid crystalline ferro-electric phases containingat least one compound of the formula I' and electro-optical displayelements comprising these phases. The preferred meanings given forformula I for R¹, R², R³, A¹, A², A³, A⁴, Z¹, Z², Z³ and p are alsovalid by analogy for compounds of the formula I'.

Of the compounds of the formula I, those stereoisomers are preferred inwhich the saturated rings (for example Cy, Dio, Dit) aretrans-1,4-disubstituted.

When ##STR5## wherein R¹ is an optically active alkoxy group with anasymmetric carbon atom, R² preferably denotes an unsubstituted orsubstituted alkyl group of 1-15 carbon atoms in which one or twonon-adjacent CH₂ groups can also be replaced by at least one member ofthe group --CO--, --O--CO--, --CO--O and --CH═CH--; F, Cl, Br, --CN--,--NCS or R³ --(A³)_(p) --Z² --.

When ##STR6## wherein R² is an optically active alkoxy group with anasymmetric carbon atom, R¹ preferably denotes an unsubstituted orsubstituted alkyl group of 1-15 carbon atoms in which one or twonon-adjacent CH₂ groups can also be replaced by --O-- or --CH═CH--. Anespecially preferred meaning of R¹ is a straight-chain alkyl or alkoxy,in particular straight-chain alkyl, each of 5-12 carbon atoms.

When ##STR7## wherein R² is an optically active alkoxy group with anasymmetric carbon atom, R¹ preferably denotes an unsubstituted orsubstituted alkyl group of 1-15 carbon atoms in which two non-adjacentCH₂ groups are replaced by --O--, --CO--, --O--CO--, --CO--O-- and/or--CH═CH--.

When ##STR8## particularly when ##STR9## the optically active radical R¹or R² preferably denotes an alkyl group in which two non-adjacent CH₂groups are replaced by at least one member of the group --O--, --CO--,--O--CO--, --CO--O and --CH═CH--. Especially preferred optically activeradicals correspond to the formula ##STR10## in which X denotes --O--,--CO--O-- or --O--CO--, Q denotes --CH₂ -- or a single bond, Y denotesCH₃ and R denotes a straight-chain alkyl of 1 to 7 carbon atoms, inwhich the CH₂ group linked to the asymmetric carbon atoms is replaced by--O--, --CO--O-- or --O--CO--.

The compounds of the formula I are prepared by methods known per se.These are described in the literature (for example in standard workssuch as Houben-Weyl, Methoden der Organischen Chemie,Georg-Thieme-Verlag, Stuttgart), under reaction conditions which areknown and suitable for the named reactions. In this context, use canalso be made of variants which are known per se and not referred to herein further detail.

The person skilled in the art can infer the corresponding synthesismethods, via routine methods, from the state of the art (for exampleGerman Offenlegungsschriften 2,344,732; 2,450,088; 2,429,093; 2,502,904;2,636,684; 2,701,591 and 2,752,975 in respect of compounds with1,4-cyclohexylene and 1,4-phenylene groups; German Patent 2,641,724 inrespect of compounds with pyrimidine-2,5-diyl groups; GermanOffenlegungsschriften 2,944,905 and 3,227,916 in respect of compoundswith 1,3-dioxane-2,5-diyl groups; East German Patent 160,061 in respectof compounds with 1,3-dithiane-2,5-diyl groups; U.S. Pat. Nos. 4,261,652and 4,219,256 in respect of compound with 1,4-bicyclo(2,2,2)-octylenegroups; and German Offenlegungsschrift 3,201,721 in respect of compoundswith --CH₂ --CH₂ bridge members).

If desired, the starting materials can also be formed in situ, in such away that they are not isolated from the reaction mixture, butimmediately reacted further to form compounds of the formula I.

In general, two corresponding partial compounds (for example (1) and (2)(Scheme 1) or (3) and (4) (Scheme 2)) are condensed to give compounds ofthe formula I: ##STR11##

--M¹ L¹ and --M² L² are condensable building blocks, which correspondto, for example, malonic acid derivatives (for example malonicdialdehyde), amidines, aldehydes, 1,3-propanediols and/or1,3-propanedithiols. L¹ L² are one or more split-off groups.

--M³ L³ and --M⁴ L⁴ are condensable building blocks, for exampleselected from the group --COOH, --COhalogen, --OH, --Ometal, --CH₂-halogen, --CH₂ -metal, --CH₂ --OH, --CH₂ --O-metal, -metal and-halogen.

L³ and L⁴ are leaving groups. L³ L⁴ is a split-off group, for example H₂O, H-halogen, metal-halogen.

In addition, to synthesize compounds of the formula I, appropriateintramolecular condensations can be carried out (for examplecondensation of 1,4-diketones with hydrazine (for example GermanOffenlegungsschrift 3,238,350) or reaction of a butadiene derivativewith, for example, actylene dicarboxylic acid derivatives (for exampleJapanese Published Applications 58-144, 327 and 58-146, 543)).

The starting materials are known or are obtainable by methods analogousto those used for the known compounds. The person skilled in the art caninfer, via routine methods, the corresponding starting materials and/ormethods for their synthesis from the state of the art.

In addition, the compounds of the formula I can be prepared by reducinga compound which otherwise corresponds to the formula I, but comprisesone or more reducible groups and/or C-C bonds in place of hydrogenatoms.

Such reducible groups are preferably carbonyl groups, in particular ketogroups, as well as, for example, free or esterified groups oraromatically bound halogen atoms. Preferred starting materials for thereduction correspond to the formula I, but can comprise, in place of acyclohexane ring, a cyclohexene ring or a cyclohexanone ring, and/or inplace of a --CH₂ CH₂ -- group a --CH═CH-group, and/or in place of a--CH₂ -group a --CO-group, and/or in place of an H atom a free orfunctionally (for example in the form of its p-toluenesulfonate)transformed OH group.

The reduction can take place by, for example, catalytic hydrogenation attemperatures between about 0° and about 200° and pressures between about1 and 200 bar in an inert solvent, for example an alcohol such asmethanol, ethanol or isopropanol (sic), an ether such as tetrahydrofuran(THF) or dioxane, an ester such as ethyl acetate, a carboxylic acid suchas acetic acid, or a hydrocarbon such as cyclohexane. Suitable catalystsare, advantageously, noble metals such as Pt or Pd which can be used inthe form of oxides (for example PtO₂, PdO), either on a carrier (forexample Pd on carbon, calcium carbonate or strontium carbonate) or infinely divided form.

Ketones can also be reduced to the corresponding compounds of theformula I, which contain alkyl groups and/or --CH₂ CH₂ -bridges, by themethod of Clemmensen (with zinc, zinc amalgam or tin and hydrochloricacid, conveniently in an aqueous alcoholic solution or in aheterogeneous phase with water/toluene at temperatures between about 80°and 120°) or that of Wolff-Kishner (with hydrazine, conveniently in thepresence of an alkali such as KOH or NaOH in a high boiling solvent suchas diethylene glycol or triethylene glycol at temperatures between about100° and 200°).

Furthermore, reductions are possible with complex hydrides. For example,arylsulfonyloxy groups can be reductively removed with LiAlH₄, inparticular p-toluenesulfonyloxymethyl groups can be reduced to methylgroups, conveniently in an inert solvent such as diethyl ether or THF attemperatures between about 0° and 100°. Double bonds can be hydrogenatedwith NaBH₄ or tributyl tin hydride in methanol (even in the presence ofCN groups!); in this way, for example 1-cyano-cyclohexene derivativesgive rise to the corresponding cyclohexane derivatives.

Esters of the formula I (R¹ and/or R² =alkyl, in which one or two CH₂groups are replaced by --O--CO-- and/or --CO--O-- groups, or Z¹ and/orZ² =--CO--O-- or --O--CO--) can also be obtained by esterification ofthe corresponding carboxylic acids (or their reactive derivatives) withalcohols or phenols (or their reactive derivatives).

Suitable reactive derivatives of the named carboxylic acids are inparticular the acid halides, especially the chlorides and bromides, aswell as the anhydrides, azides or esters, in particular alkyl esterswith 1-4 carbon atoms in the alkyl group.

Suitable reactive derivatives of the named alcohols or phenols are inparticular the corresponding metal alcoholates or phenolates, inparticular those of an alkali metal such as Na or K.

The esterification is preferably carried out in the presence of an inertsolvent. Suitable solvents are especially ethers such as diethyl ether,di-n-butyl ether, THF, dioxane or anisole; ketones such as acetone,butanone or cyclohexanone; amides such as DMF or phosphoric acidhexamethyltriamide; hydrocarbons such as benzene, toluene or xylene;halogenated hydrocarbons such as carbon tetrachloride ortetrachloroethylene, and sulfoxides such as dimethyl sulfoxide orsulfolane. Solvents not miscible with water can at the same time beadvantageously used for distilling off azeotropically water formed inthe esterification. In some cases, an excess of an organic base, forexample pyridine, quinoline or triethylamine, can be used as solvent forthe esterification. The esterification can also be carried out in theabsence of a solvent, for example by simply heating the components inthe presence of sodium acetate. The reaction temperature is usuallybetween -50° and +250°, preferably between -20° and +80°. At thesetemperatures, the esterification reactions are usually terminated after15 minutes to 48 hours.

Individually, the reaction conditions for the esterification depend to alarge extent on the type of the starting materials used. Thus, a freecarboxylic acid is reacted with a free alcohol or phenol usually in thepresence of a strong acid, for example a mineral acid such ashydrochloric acid or sulfuric acid. A preferred reaction method is thereaction of an acid anhydride and especially an acid chloride with analcohol, preferably in an alkaline medium, using as the bases especiallyalkali metal hydroxides, such as sodium or potassium hydroxide, alkalimetal carbonates or bicarbonates such as sodium carbonate, sodiumbicarbonate, potassium carbonate or potassium bicarbonate; alkali metalacetates such as sodium or potassium acetate; alkaline earth metalhydroxides such as calcium hydroxide; or organic bases such astriethylamine, pyridine, lutidine, collidine or quinoline. Anotherpreferred embodiment of the esterification consists in first convertingthe alcohol or phenol to the sodium or potassium alcoholate orphenolate, for example by treatment with ethanolic sodium or potassiumhydroxide solution, isolating the alcoholate or phenolate, suspending ittogether with sodium bicarbonate or potassium carbonate in acetone ordiethyl ether with stirring, and treating this suspension with asolution of the acid chloride or anhydride in diethyl ether, acetone orDMF, conveniently at temperatures between about -25° and +20°.

Dioxane or dithiane derivatives of the formula I (in which one of thegroups A¹ and/or A² and/or A³ represents a 1,3-dioxane-2,5-diyl group ora 1,3-dithiane-2,5-diyl group) are conveniently prepared by reacting acorresponding aldehyde with a corresponding 1,3-diol or a corresponding1,3-dithiol (or one of its reactive derivatives), preferably in thepresence of an inert solvent such as benzene or toluene, and/or acatalyst, for example a strong acid such as sulfuric acid,benzenesulfonic or p-toluenesulfonic acid, at temperatures between about20° and about 150°, preferably between 80° and 120°. The most suitablereactive derivatives of the starting materials are the acetals.

The aldehydes, 1,3-diols and 1,3-dithiols mentioned as well as theirreactive derivatives are partly known, and partly can be preparedwithout difficulties by standard procedures of organic chemistry on thebasis of compounds known in the literature. For example, aldehydes areobtainable by oxidation of the corresponding carboxylic acids or theirderivatives, the diols by reduction of the corresponding diesters, anddithiols by reacting the corresponding dihalides with NaSH.

To prepare nitriles of the formula I (in which R¹ and/or R² are CN), thecorresponding acid amides can be dehydrated. For example, the amides areobtainable from the corresponding esters or acid halides by reactionwith ammonia. Suitable dehydrating agents are, for example, inorganicacid chlorides such as SOCl₂, PCl₃, PCl₅, POCl₃, SO₂ Cl₂, COCl₂, as wellas P₂ O₅, P₂ S₅, AlCl₃ (for example as a double bond (sic) with NaCl),aromatic sulfonic acids and sulfonic acid halides. The reaction can takeplace in the presence or absence of an inert solvent at temperaturesbetween about 0° and 150°; suitable solvents are, for example, basessuch as pyridine or triethylamine, aromatic hydrocarbons such asbenzene, toluene or xylene, or amides such as DMF.

To prepare the nitriles of the formula I mentioned above, thecorresponding acid halides, preferably the chlorides, can be reactedwith sulfamide, conveniently in an inert solvent such astetramethylenesulfone, at temperatures between about 80° and 150°,preferably at 120°. The nitriles can be isolated direct after the usualworking up.

Ethers of the formula I (in which R¹ and/or R² are an alkyl group inwhich one or two CH₂ groups are replaced by O atoms, and/or in which Z¹and/or Z² is an --OCH₂ or a --CH₂ O-- group) are obtainable by anetherification of the corresponding hydroxy compounds, preferably thecorresponding phenols, in which the hydroxy compound is convenientlyfirst converted to a corresponding metal derivative, for example to thecorresponding alkali metal alcoholate or alkali metal phenolate, bytreatment with NaH, NaNH₂, NaOH, KOH, Na₂ CO₃ or K₂ CO₃. The alcoholateor phenolate can be reacted with the corresponding alkyl halide,alkylsulfonate or dialkylsulfate, conveniently in an inert solvent suchas acetone, 1,2-dimethoxyethane, DMF or dimethyl sulfoxide or an excessof aqueous or aqueous-alcoholic NaOH or KOH at temperatures betweenabout 20° and 100°.

The ferroelectric liquid crystalline phases according to the inventionconsist of 2 to 15, preferably 3 to 12 components, of which at least oneis a compound of the formula I. The other components are preferablyselected from compounds of the formulae II to IV, ##STR12## in which R⁴and R⁵ each independently of one another are n-alkyl of 5 to 12 carbonatoms, and R⁶, R⁷, R⁸ and R⁹, each independently of one another, arestraight-chain or branched, if desired chiral, alkyl, alkoxy,alkoxycarbonyl or alkanoyloxy groups of 5 to 12, especially of 6 to 10carbon atoms. Ring A is 1,4-phenylene or trans-1,4-cyclohexylene. n is 0or 1.

All these substances can be prepared in accordance with methods knownfrom the literature.

In addition, the preferred ferroelectric phases according to theinvention contain at least one compound of the formula V

    R.sup.1 --Q.sup.1 --A--(Q.sup.2).sub.q --R.sup.2           V

in which

R¹ and R² each independently of one another are a straight-chain alkylgroup of 1 to 15 carbon atoms, in which one or more non-adjacent CH₂groups can also be replaced by --O--, --S--, --CO--, CHCH₃ --O--,--CHCH₃ --, --CH--halogen--, CHCN--, --O--CO--, --O--COO--, --CO--O--and/or --CH═CH--,

A is ##STR13## q is 0 or 1, Q¹ and Q² each independently of one anotherare --(A⁰ --Z⁰)_(p) --, in which

A⁰ is 1,4-cyclohexylene which is unsubstituted or mono- orpolysubstituted by halogen atoms, CH₃ -- and/or nitrile groups, in whichone or two non-adjacent CH₂ -- groups can also be replaced by --O--and/or --S-- and/or a ##STR14## grouping can be replaced by ##STR15## oris, 1,4-phenylene which is unsubstituted or mono- or polysubstituted byhalogen atoms, CH₃ -- and/or nitrile groups, in which one or more CH--groups can also be replaced by N (Ph), one of the radicals A⁰ also being2,6-naphthylene (Na) or tetrahydro-2,6-naphthylene (4H--Na), if desiredsubstituted by halogen or CN,

Z⁰, Z¹ and Z² each independently of one another are --CO--O--,--O--CO--, --CH₂ O--, OCH₂ --, --CH₂ CH₂ --, --CHCNCH₂ --, --CH₂--CHCN-- or a single bond, and

p is 1, 2 or 3, or is O if A denotes tetra- or octaphenanthrene, and ifA= ##STR16## at least one group Z⁰ is --CHCNCH₂ -- or --CH₂ CHCN--and/or in at least one of the groups R¹ and R², at least one CH₂ groupis substituted by --CHCN--.

The compounds of the formula V can possess straight-chain or branchedwing groups R¹ and/or R². Compounds with branched wing groups can beused in the form of the racemate or as optically active compounds.Achiral base mixtures of compounds of the formula V and, if desired,further achiral components, can be doped with chiral compounds of theformula I or, additionally, with other chiral compounds, in order toobtain chirally tilted smectic phases.

Smaller groups of compounds which are especially preferred are those ofthe formulae V1 to V18: ##STR17##

A further smaller group of compounds which is especially preferred isthat of the formulae V19 to V22:

    R.sup.1 --A.sup.0 --Cy-(CH.sub.2).sub.r --CHCN--C.sub.s H.sub.2s+1V 19

    R.sup.1 --A.sup.0 --A.sup.0 --Cy-(CH.sub.2).sub.r --CHCN--C.sub.s H.sub.2s+1V 20

    R.sup.1 --A.sup.0 --A.sup.0 --CHCN--CH.sub.2 --Cy-R.sup.2  V 21

    R.sup.1 --A.sup.0 --A.sup.0 --CH.sub.2 --CHCN--Cy-R.sup.2  V 22

in which r is 0, 1, 2 or 3 and (r+s) is 1 to 14.

Compounds of the formula V which do not exhibit any S_(c) phases, arealso suitable as components of smectic phases according to theinvention.

Compounds of the formula V which are especially preferred are givenbelow:

4-(4-Cyano-4-butylcyclohexyl)-4'-heptylbiphenyl, m.p. 56°, c.p. 122°

4-(4-Cyano-4-butylcyclohexyl)-4'-octylbiphenyl, m.p. 42°, c.p. 118°

4-(4-Cyano-4-butylcyclohexyl)-4'-nonylbiphenyl

4-(4-Cyano-4-butylcyclohexyl)-4'-butoxybiphenyl

4-(4-Cyano-4-butylcyclohexyl)-4'-pentoxybiphenyl

4-(4-Cyano-4-butylcyclohexyl)-4'-hexoxybiphenyl

4-(4-Cyano-4-butylcyclohexyl)-4'-heptoxybiphenyl, m.p. 93°, c.p. 156°

4-(4-Cyano-4-butylcyclohexyl)-4'-octoxybiphenyl, m.p. 80°, c.p. 154°

4-(4-Cyano-4-butylcyclohexyl)-4'-nonoxybiphenyl, m.p. 89°, c.p. 150°

4-(4-Cyano-4-pentylcyclohexyl)-4'-ethylbiphenyl

4-(4-Cyano-4-pentylcyclohexyl)-4'-propylbiphenyl

4-(4-Cyano-4-pentylcyclohexyl)-4'-butylbiphenyl, m.p. 75°, c.p. 128°

4-(4-Cyano-4-pentylcyclohexyl)-4'-pentylbiphenyl

4-(4-Cyano-4-pentylcyclohexyl)-4'-hexylbiphenyl

4-(4-Cyano-4-pentylcyclohexyl)-4'-heptylbiphenyl, m.p. 54°, c.p. 127°

4-(4-Cyano-4-pentylcyclohexyl)-4'-octylbiphenyl, m.p. 43°, c.p. 115°

4-(4-Cyano-4-pentylcyclohexyl)-4'-nonylbiphenyl

4-(4-Cyano-4-pentylcyclohexyl)-4'-butoxybiphenyl

4-(4-Cyano-4-pentylcyclohexyl)-4'-pentoxybiphenyl

4-(4-Cyano-4-pentylcyclohexyl)-4'-hexoxybiphenyl

4-(4-Cyano-4-pentylcyclohexyl)-4'-heptoxybiphenyl, m.p. 91°, c.p. 161°

4-(4-Cyano-4-pentylcyclohexyl)-4'-octyloxybiphenyl, m.p. 93°, c.p. 160°

4-(4-Cyano-4-pentylcyclohexyl)-4'-nonoxybiphenyl, m.p. 83°, c.p. 156°

4-[4-Cyano-4-(2-methylbutylcyclohexyl)]-4'-ethylbiphenyl

4-[4-Cyano-4-(2-methylbutylcyclohexyl)]-4'-propylbiphenyl

4-[4-Cyano-4-(2-methylbutylcyclohexyl)]-4'-butylbiphenyl

4-[4-Cyano-4-(2-methylbutylcyclohexyl)]-4'-pentylbiphenyl

4-[4-Cyano-4-(2-methylbutylcyclohexyl)]-4'-hexylbiphenyl

4-[4-Cyano-4-(2-methylbutylcyclohexyl)]-4'-heptylbiphenyl

4-[4-Cyano-4-(2-methylbutylcyclohexyl)]-4'-octylbiphenyl

4-[4-Cyano-4-(2-methylbutylcyclohexyl)]-4'-nonylbiphenyl

4-[4-Cyano-4-(2-methylbutylcyclohexyl)]-4'-butoxybiphenyl

4-[4-Cyano-4-(2-methylbutylcyclohexyl)]-4'-pentoxybiphenyl

4-[4-Cyano-4-(2-methylbutylcyclohexyl)]-4'-hexoxybiphenyl

4-[4-Cyano-4-(2-methylbutylcyclohexyl)]-4'-heptoxybiphenyl, m.p. 66°,c.p. 131.4°, c.p. 131.0° Ch/Bp

4-[4-Cyano-4-(2-methylbutylcyclohexyl)]-4'-octyloxybiphenyl

4-[4-Cyano-4-(2-methylbutylcyclohexyl)]-4'-nonoxybiphenyl,

4-(4-Cyano-4-hexylcyclohexyl)-4'-propylbiphenyl

4-(4-Cyano-4-hexylcyclohexyl)-4'-butylbiphenyl

4-(4-Cyano-4-hexylcyclohexyl)-4'-pentylbiphenyl

4-(4-Cyano-4-hexylcyclohexyl)-4'-hexylbiphenyl

4-(4-Cyano-4-hexylcyclohexyl)-4'-heptylbiphenyl, m.p. 66°, c.p. 125°

4-(4-Cyano-4-hexylcyclohexyl)-4'-octylbiphenyl

4-(4-Cyano-4-hexylcyclohexyl)-4'-nonylbiphenyl

4-(4-Cyano-4-hexylcyclohexyl)-4'-butoxybiphenyl

4-(4-Cyano-4-hexylcyclohexyl)-4'-pentoxybiphenyl

4-(4-Cyano-4-hexylcyclohexyl)-4'-hexoxybiphenyl

4-(4-Cyano-4-hexylcyclohexyl)-4'-heptoxybiphenyl, m.p. 88°, c.p. 156°

4-(4-Cyano-4-hexylcyclohexyl)-4'-octoxybiphenyl, m.p. 90°, c.p. 155°

4-(4-Cyano-4-hexylcyclohexyl)-4'-nonoxybiphenyl, m.p. 87°, c.p. 152°

4-(4-Cyano-4-heptylcyclohexyl)-4'-ethylbiphenyl

4-(4-Cyano-4-heptylcyclohexyl)-4'-propylbiphenyl

4-(4-Cyano-4-heptylcyclohexyl)-4'-butylbiphenyl

4-(4-Cyano-4-heptylcyclohexyl)-4'-pentylbiphenyl

4-(4-Cyano-4-heptylcyclohexyl)-4'-hexylbiphenyl

4-(4-Cyano-4-heptylcyclohexyl)-4'-heptylbiphenyl, m.p. 61°, c.p. 124°

4-(4-Cyano-4-heptylcyclohexyl)-4'-octylbiphenyl, m.p. 64°, c.p. 125°

4-(4-Cyano-4-heptylcyclohexyl)-4'-nonylbiphenyl

4-(4-Cyano-4-heptylcyclohexyl)-4'-butoxybiphenyl

4-(4-Cyano-4-heptylcyclohexyl)-4'-pentoxybiphenyl

4-(4-Cyano-4-heptylcyclohexyl)-4'-hexoxybiphenyl

4-(4-Cyano-4-heptylcyclohexyl)-4'-heptoxybiphenyl, m.p. 87°, c.p. 155°

4-(4-Cyano-4-heptylcyclohexyl)-4'-octoxybiphenyl, m.p. 83°, c.p. 154°

4-(4-Cyano-4-heptylcyclohexyl)-4'-nonoxybiphenyl, m.p. 81°, c.p. 152°

4-(4-Cyano-4-octylcyclohexyl)-4'-ethylbiphenyl

4-(4-Cyano-4-octylcyclohexyl)-4'-propylbiphenyl

4-(4-Cyano-4-octylcyclohexyl)-4'-butylbiphenyl

4-(4-Cyano-4-octylcyclohexyl)-4'-pentylbiphenyl, m.p. 52°, c.p. 124°

4-(4-Cyano-4-octylcyclohexyl)-4'-hexylbiphenyl

4-(4-Cyano-4-octylcyclohexyl)-4'-heptylbiphenyl, m.p. 61°, c.p. 122°

4-(4-Cyano-4-octylcyclohexyl)-4'-octylbiphenyl, m.p. 65°, c.p. 125°

4-(4-Cyano-4-octylcyclohexyl)-4'-nonylbiphenyl

4-(4-Cyano-4-octylcyclohexyl)-4'-butoxybiphenyl

4-(4-Cyano-4-octylcyclohexyl)-4'-pentoxybiphenyl

4-(4-Cyano-4-octylcyclohexyl)-4'-hexoxybiphenyl

4-(4-Cyano-4-octylcyclohexyl)-4'-heptoxybiphenyl, m.p. 85°, c.p. 151°

4-(4-Cyano-4-octylcyclohexyl)-4'-octoxybiphenyl, m.p. 81°, c.p. 150°

4-(4-Cyano-4-octylcyclohexyl)-4'-nonoxybiphenyl, m.p. 72°, c.p. 149°

4-(4-Cyano-4-nonylcyclohexyl)-4'-ethylbiphenyl

4-(4-Cyano-4-nonylcyclohexyl)-4'-propylbiphenyl

4-(4-Cyano-4-nonylcyclohexyl)-4'-butylbiphenyl

4-(4-Cyano-4-nonylcyclohexyl)-4'-pentylbiphenyl

4-(4-Cyano-4-nonylcyclohexyl)-4'-heptylbiphenyl

4-(4-Cyano-4-nonylcyclohexyl)-4'-octylbiphenyl

4-(4-Cyano-4-nonylcyclohexyl)-4'-nonylbiphenyl

4-(4-Cyano-4-nonylcyclohexyl)-4'-butoxybiphenyl

4-(4-Cyano-4-nonylcyclohexyl)-4'-pentoxybiphenyl

4-(4-Cyano-4-nonylcyclohexyl)-4'-hexoxybiphenyl

4-(4-Cyano-4-nonylcyclohexyl)-4'-heptoxybiphenyl

4-(4-Cyano-4-nonylcyclohexyl)-4'-octoxybiphenyl

4-(4-Cyano-4-nonylcyclohexyl)-4'-nonoxybiphenyl

All compounds of the formula V are prepared by methods known per se, asdescribed in the literature for example in standard works such asHouben-Weyl, Methoden der Organischen Chemie, (Methods of OrganicChemistry), Georg-Thieme-Verlag, Stuttgart), under reaction conditionswhich are known and suitable for the reactions mentioned. In thiscontext, use can also be made of variants which are known per se and arenot referred to here in further detail.

For the most part, formula V comprises known compounds, for example thepreferred compounds described in German Offenlegungsschrift 3,231,707,3,319,781, 3,320,024, 3,407,013, 3,443,029, 3,332,690, 3,332,691,3,332,692, 2,933,563, 2,853,728, 2,613,293, 3,401,320, 3,136,624,3,040,632, 3,205,766, 2,240,864, 2,937,700, 3,410,734, 3,324,686, EP-OS0,085,995, EP-OS 0,084,194, East German Patent 116,732, French PatentSpecifications 2,425,469 and 2,419,966, U.S. Pat. No. 4,237,026,3,953,491 and 4,225,454 and in H. J. Deutscher et al., J. prakt. Chemie,321, 569 (1979) and J. C. Dubois et al. Mol Cryst. Liq. Cryst. 47, 193(1978).

Further components of the phases according to the invention may becompounds of the formula ##STR18## in which R¹ and R² have the meaninggiven in Formula V.

Chirally tilted smectic liquid crystalline phases according to theinvention, the achiral base mixture of which contains, in addition tocompounds of the formula I, at least one other component with negativeor small positive dielectric anisotropy, are especially preferred. Othersuitable components with small positive or negative dielectricanisotropy, are compounds of the partial formulae Va to Vp: ##STR19##

R⁴ and R⁵ each are preferably straight-chain alkyl, alkoxy, alkanoyloxyor alkoxycarbonyl of, in each case, 3 to 12 carbon atoms. X ispreferably 0. n is 0 or 1.

The compounds of the partial formulae Va, Vb, Vd and Vf, in which R⁴ andR⁵ each are straight-chain alkyl or alkoxy of, in each case, 5 to 10carbon atoms, are particularly preferred.

The compounds of the partial formulae Vc, Vh and Vi are suitable asmelting point-depressing additives and they are normally added to thebasic mixtures in amounts not greater than 5%, preferably 1 to 3%. R⁴and R⁵ in the compounds of the partial formulae Vc, Vh and Vi are,preferably, straight-chain alkyl of 2 to 7, preferably 3 to 5, carbonatoms. Another class of compounds suitable as melting point depressantsin the phases according to the invention, is that of the formula##STR20## in which R⁴ and R⁵ have the preferred meaning indicated forVc, Vh and Vi.

Other suitable components with a negative dielectric anisotropy arecompounds comprising the structural element B or C. ##STR21##

Preferred compounds of this type correspond to the formulae VIb and VIc:##STR22##

R' and R" each are preferably straight-chain alkyl or alkoxy groups of,in each case, 2 to 10 carbon atoms. Q¹ and Q² each are 1,4-phenylene,trans-1,4-cyclohexylene 4,4'-biphenylyl, 4-(trans-4-cyclohexyl)phenyl,trans,trans-4,4'-bicyclohexyl, or one of the groups Q¹ and Q² is also asingle bond.

Q³ and Q⁴ each are 1,4-phenylene, 4,4'-biphenylyl ortrans-1,4-cyclohexylene. One of the groups Q³ and Q⁴ can also be1,4-phenylene, in which at least one CH group is replaced by N. R"' isan optically active radical with an asymmetric carbon atom of thestructure ##STR23##

Particularly preferred compounds of the formula VIc are those of theformula VIc': ##STR24## in which A is 1,4-phenylene ortrans-1,4-cyclohexylene, and n is 0 or 1.

The phases according to the invention contain about 0.5-40%, preferably5-10%, of one or more compounds of the formula I.

Phases according to the invention, containing 0.3-5%, preferably 1-4%,of one or more compounds of the formula I, are furthermore preferred.

The preparation of the dielectrics according to the invention is carriedout in the usual manner. The components are usually dissolved in oneanother, conveniently at elevated temperature.

The liquid crystalline phases according to the invention can be modifiedby suitable additions in such a manner that they can be utilized in alltypes of liquid crystal display elements known so far.

The examples below are intended to illustrate the invention withoutlimiting it. M.p.=melting point, c.p.=clear point. All percentages,whether those above or those below, are percentage by weight; alltemperatures are given in degrees Celsius. The values for thespontaneous polarization are valid at room temperature. Other meaningsare: K:crystalline-solid state, S:smectic phase (the suffix indicatesthe type of phase), N:nematic state, CH:cholestric phase, I:isotropicphase. The number situated between two symbols indicates the transitiontemperatures in degrees Celsius. "Usual working up" means the following:the mixture is treated with water and extracted with methylene chloride,the phases are separated, the organic phase is dried, evaporated and theproduct is purified by crystallization and/or chromatography.

EXAMPLE 1

A solution of 15.2 g of 4-(5-n-nonylpyrimid-2-yl)-phenol, 5.5 g ofR-2-chloropropionic acid and 0.62 g of 4-N,N-dimethylaminopyridine in100 ml of dichloromethane is slowly treated at 0° with a solution of11.6 g of dicyclohexylcarbodiimide in 6 ml of dichloromethane; themixture is warmed to room temperature and stirred for a further 2 hours.After filtering off the separated urea derivative, the filtrate iswashed with dilute hydrochloric acid and water, and the organic phase isworked up in the usual way. R-4-(5-n-nonylpyrimid-2-yl)-phenyl2-chloropropionate, m.p. 69°, is obtained.

The optically active compounds listed below are prepared in an analogousmanner by esterification or etherification in accordance with a methodknown from the literature:

2-p-(2-Methylbutoxyphenyl)-5-butylpyrimidine

2-p-(2-Methylbutoxyphenyl)-5-pentylpyrimidine

2-p-(2-Methylbutoxyphenyl)-5-hexylpyrimidine

2-p-(2-Methylbutoxyphenyl)-5-heptylpyrimidine

2-p-(2-Methylbutoxyphenyl)-5-octylpyrimidine

2-p-(2-Methylbutoxyphenyl)-5-nonylpyrimidine

2-p-(2-Methylbutoxyphenyl)-5-decylpyrimidine

2-p-(2-Methylbutoxyphenyl)-5-undecylpyrimidine, m.p. 40°, c.p. 47°,S_(C*) /S_(A*) 41°

2-p-(2-Methylbutoxyphenyl)-5-dodecylpyrimidine

2-p-(2-Methylbutoxyphenyl)-5-heptoxymethylpyrimidine

2-p-(2-Methylbutoxyphenyl)-5-hexoxyethylpyrimidine

2-p-(2-Methylbutoxyphenyl)-5-pentoxypropylpyrimidine

2-p-(3-Methylpentoxyphenyl)-5-butylpyrimidine

2-p-(3-Methylpentoxyphenyl)-5-pentylpyrimidine

2-p-(3-Methylpentoxyphenyl)-5-hexylpyrimidine, m.p. 13°, c.p. 32°

2-p-(3-Methylpentoxyphenyl)-5-heptylpyrimidine, m.p. 39°

2-p-(3-Methylpentoxyphenyl)-5-octylpyrimidine, m.p. 36°

2-p-(3-Methylpentoxyphenyl)-5-nonylpyrimidine, m.p. 23°, c.p. 46° S_(C*)/S_(A*) 39°

2-p-(3-Methylpentoxyphenyl)-5-decylpyrimidine, m.p. 22°, c.p. 41°

2-p-(3-Methylpentoxyphenyl)-5-undecylpyrimidine, m.p. 25°, c.p. 50°,S_(C*) /S_(A*) 45°

2-p-(3-Methylpentoxyphenyl)-5-dodecylpyrimidine, m.p. 28°, c.p. 51°,S_(C*) /S_(A*) 47°

2-p-(3-Methylpentoxyphenyl)-5-heptoxymethylpyrimidine

2-p-(3-Methylpentoxyphenyl)-5-hexoxyethylpyrimidine

2-p-(3-Methylpentoxyphenyl)-5-pentoxypropylpyrimidine

2-p-(4-Methylhexoxyphenyl)-5-butylpyrimidine

2-p-(4-Methylhexoxyphenyl)-5-pentylpyrimidine

2-p-(4-Methylhexoxyphenyl)-5-hexylpyrimidine, m.p. 25°, c.p. 42°

2-p-(4-Methylhexoxyphenyl)-5-heptylpyrimidine, m.p. 28.5°, c.p. 60°,S_(C*) /S_(A*) 54°

2-p-(4-Methylhexoxyphenyl)-5-octylpyrimidine, m.p. 31°, c.p. 51°, S_(C*)/S_(A*) 47°

2-p-(4-Methylhexoxyphenyl)-5-nonylpyrimidine, m.p. 23°, c.p. 52°, S_(C*)/S_(A*) 30°

2-p-(4-Methylhexoxyphenyl)-5-decylpyrimidine, m.p. 33°, c.p. 58°

2-p-(4-Methylhexoxyphenyl)-5-undecylpyrimidine, m.p. 36°, c.p. 60°

2-p-(4-Methylhexoxyphenyl)-5-dodecylpyrimidine, m.p. 41°, c.p. 52°

2-p-(4-Methylhexoxyphenyl)-5-heptoxymethylpyrimidine

2-p-(4-Methylhexoxyphenyl)-5-hexoxyethylpyrimidine

2-p-(4-Methylhexoxyphenyl)-5-pentoxypropylpyrimidine

2-p-(5-Methylheptoxyphenyl)-5-butylpyrimidine

2-p-(5-Methylheptoxyphenyl)-5-pentylpyrimidine

2-p-(5-Methylheptoxyphenyl)-5-hexylpyrimidine, m.p. -5°, c.p. 42°

2-p-(5-Methylheptoxyphenyl)-5-heptylpyrimidine, m.p. -6°, c.p. 49°

2-p-(5-Methylheptoxyphenyl)-5-octylpyrimidine, m.p. 12°, c.p. 50°,S_(C*) /S_(A*) 35°

2-p-(5-Methylheptoxyphenyl)-5-nonylpyrimidine, m.p. 10°, c.p. 59°,S_(C*) /S_(A*) 46°

2-p-(5-Methylheptoxyphenyl)-5-decylpyrimidine, m.p. 17°, c.p. 63°,S_(C*) /S_(A*) 54°

2-p-(5-Methylheptoxyphenyl)-5-undecylpyrimidine, m.p. 20°, c.p. 59°

2-p-(5-Methylheptoxyphenyl)-5-dodecylpyrimidine, m.p. 23°, c.p. 61°

2-p-(5-Methylheptoxyphenyl)-5-heptoxymethylpyrimidine

2-p-(5-Methylheptoxyphenyl)-5-hexoxyethylpyrimidine

2-p-(5-Methylheptoxyphenyl)-5-pentoxypropylpyrimidine

2-p-(6-Methyloctoxyphenyl)-5-butylpyrimidine

2-p-(6-Methyloctoxyphenyl)-5-pentylpyrimidine

2-p-(6-Methyloctoxyphenyl)-5-hexylpyrimidine, m.p. 12°, c.p. 46°

2-p-(6-Methyloctoxyphenyl)-5-heptylpyrimidine, m.p. 10°, c.p. 61°,S_(C*) /S_(A*) 39°

2-p-(6-Methyloctoxyphenyl)-5-octylpyrimidine, m.p. 3°, c.p. 56°, S_(C*)/S_(A*) 49°

2-p-(6-Methyloctoxyphenyl)-5-nonylpyrimidine, m.p. 16°, c.p. 61°, S_(C*)/S_(A*) 49°

2-p-(6-Methyloctoxyphenyl)-5-decylpyrimidine, m.p. 41°, c.p. 61°

2-p-(6-Methyloctoxyphenyl)-5-undecylpyrimidine

2-p-(6-Methyloctoxyphenyl)-5-dodecylpyrimidine, m.p. 40°, c.p. 70°

2-p-(6-Methyloctoxyphenyl)-5-heptoxymethylpyrimidine

2-p-(6-Methyloctoxyphenyl)-5-hexoxyethylpyrimidine

2-p-(6-Methyloctoxyphenyl)-5-pentoxypropylpyrimidine

2-p-(2-Methylbutyryloxyphenyl)-5-butylpyrimidine

2-p-(2-Methylbutyryloxyphenyl)-5-pentylpyrimidine

2-p-(2-Methylbutyryloxyphenyl)-5-hexylpyrimidine

2-p-(2-Methylbutyryloxyphenyl)-5-heptylpyrimidine

2-p-(2-Methylbutyryloxyphenyl)-5-octylpyrimidine

2-p-(2-Methylbutyryloxyphenyl)-5-nonylpyrimidine

2-p-(2-Methylbutyryloxyphenyl)-5-decylpyrimidine

2-p-(2-Methylbutyryloxyphenyl)-5-undecylpyrimidine, m.p. 52°

2-p-(2-Methylbutyryloxyphenyl)-5-dodecylpyrimidine

2-p-(2-Methylbutyryloxyphenyl)-5-heptoxymethylpyrimidine

2-p-(2-Methylbutyryloxyphenyl)-5-hexoxyethylpyrimidine

2-p-(2-Methylbutyryloxyphenyl)-5-pentoxypropylpyrimidine

2-p-(4-Methylhexanoyloxyphenyl)-5-butylpyrimidine

2-p-(4-Methylhexanoyloxyphenyl)-5-pentylpyrimidine

2-p-(4-Methylhexanoyloxyphenyl)-5-hexylpyrimidine

2-p-(4-Methylhexanoyloxyphenyl)-5-heptylpyrimidine

2-p-(4-Methylhexanoyloxyphenyl)-5-octylpyrimidine, m.p. 54°

2-p-(4-Methylhexanoyloxyphenyl)-5-nonylpyrimidine

2-p-(4-Methylhexanoyloxyphenyl)-5-decylpyrimidine

2-p-(4-Methylhexanoyloxyphenyl)-5-undecylpyrimidine, m.p. 38°, c.p. 50°

2-p-(4-Methylhexanoyloxyphenyl)-5-dodecylpyrimidine

2-p-(4-Methylhexanoyloxyphenyl)-5-heptoxymethylpyrimidine

2-p-(4-Methylhexanoyloxyphenyl)-5-hexoxyethylpyrimidine

2-p-(4-Methylhexanoyloxyphenyl)-5-pentoxypropylpyrimidine

2-p-(6-Methyloctanoyloxyphenyl)-5-butylpyrimidine

2-p-(6-Methyloctanoyloxyphenyl)-5-pentylpyrimidine

2-p-(6-Methyloctanoyloxyphenyl)-5-hexylpyrimidine

2-p-(6-Methyloctanoyloxyphenyl)-5-heptylpyrimidine

2-p-(6-Methyloctanoyloxyphenyl)-5-octylpyrimidine, m.p. 38°, c.p. 45°

2-p-(6-Methyloctanoyloxyphenyl)-5-nonylpyrimidine

2-p-(6-Methyloctanoyloxyphenyl)-5-decylpyrimidine

2-p-(6-Methyloctanoyloxyphenyl)-5-undecylpyrimidine, m.p. 62°

2-p-(6-Methyloctanoyloxyphenyl)-5-dodecylpyrimidine

2-p-(6-Methyloctanoyloxyphenyl)-5-heptoxymethylpyrimidine

2-p-(6-Methyloctanoyloxyphenyl)-5-hexoxyethylpyrimidine

2-p-(6-Methyloctanoyloxyphenyl)-5-pentoxypropylpyrimidine

2-p-(6-Methyloctanoylphenyl)-5-butylpyrimidine

2-p-(6-Methyloctanoylphenyl)-5-pentylpyrimidine

2-p-(6-Methyloctanoylphenyl)-5-hexylpyrimidine

2-p-(6-Methyloctanoylphenyl)-5-heptylpyrimidine

2-p-(6-Methyloctanoylphenyl)-5-octylpyrimidine, m.p. 67°, c.p. 79°

2-p-(6-Methyloctanoylphenyl)-5-nonylpyrimidine

2-p-(6-Methyloctanoylphenyl)-5-decylpyrimidine

2-p-(6-Methyloctanoylphenyl)-5-undecylpyrimidine

2-p-(6-Methyloctanoylphenyl)-5-dodecylpyrimidine

2-p-(6-Methyloctanoylphenyl)-5-heptoxymethylpyrimidine

2-p-(6-Methyloctanoylphenyl)-5-hexoxyethylpyrimidine

2-p-(6-Methyloctanoylphenyl)-5-pentoxypropylpyrimidine

2-p-(3-Chloropentoxyphenyl)-5-butylpyrimidine

2-p-(3-Chloropentoxyphenyl)-5-pentylpyrimidine

2-p-(3-Chloropentoxyphenyl)-5-hexylpyrimidine

2-p-(3-Chloropentoxyphenyl)-5-heptylpyrimidine

2-p-(3-Chloropentoxyphenyl)-5-octylpyrimidine, m.p. 15°, c.p. 43°

2-p-(3-Chloropentoxyphenyl)-5-nonylpyrimidine

2-p-(3-Chloropentoxyphenyl)-5-decylpyrimidine

2-p-(3-Chloropentoxyphenyl)-5-undecylpyrimidine

2-p-(3-Chloropentoxyphenyl)-5-dodecylpyrimidine

2-p-(3-Chloropentoxyphenyl)-5-heptoxymethylpyrimidine

2-p-(3-Chloropentoxyphenyl)-5-hexoxyethylpyrimidine

2-p-(3-Chloropentoxyphenyl)-5-pentoxypropylpyrimidine

2-p-(3-Cyanopentoxyphenyl)-5-butylpyrimidine

2-p-(3-Cyanopentoxyphenyl)-5-pentylpyrimidine

2-p-(3-Cyanopentoxyphenyl)-5-hexylpyrimidine

2-p-(3-Cyanopentoxyphenyl)-5-heptylpyrimidine

2-p-(3-Cyanopentoxyphenyl)-5-octylpyrimidine

2-p-(3-Cyanopentoxyphenyl)-5-nonylpyrimidine

2-p-(3-Cyanopentoxyphenyl)-5-decylpyrimidine

2-p-(3-Cyanopentoxyphenyl)-5-undecylpyrimidine, m.p. 60°

2-p-(3-Cyanopentoxyphenyl)-5-dodecylpyrimidine

2-p-(3-Cyanopentoxyphenyl)-5-heptoxymethylpyrimidine

2-p-(3-Cyanopentoxyphenyl)-5-hexoxyethylpyrimidine

2-p-(3-Cyanopentoxyphenyl)-5-pentoxypropylpyrimidine

2-p-(1,6-Dioxa-8-methyldecylphenyl)-5-butylpyrimidine

2-p-(1,6-Dioxa-8-methyldecylphenyl)-5-pentylpyrimidine

2-p-(1,6-Dioxa-8-methyldecylphenyl)-5-hexylpyrimidine, m.p. -8°, c.p.-28°

2-p-(1,6-Dioxa-8-methyldecylphenyl)-5-heptylpyrimidine

2-p-(1,6-Dioxa-8-methyldecylphenyl)-5-octylpyrimidine, m.p. 1°, c.p. 42°

2-p-(1,6-Dioxa-8-methyldecylphenyl)-5-nonylpyrimidine

2-p-(1,6-Dioxa-8-methyldecylphenyl)-5-decylpyrimidine m.p. 16°, c.p. 52°

2-p-(1,6-Dioxa-8-methyldecylphenyl)-5-undecylpyrimidine

2-p-(1,6-Dioxa-8-methyldecylphenyl)-5-dodecylpyrimidine

2-p-(1,6-Dioxa-8-methyldecylphenyl)-5-heptoxymethylpyrimidine

2-p-(1,6-Dioxa-8-methyldecylphenyl)-5-hexoxyethylpyrimidine

2-p-(1,6-Dioxa-8-methyldecylphenyl)-5-pentoxypropylpyrimidine

2-p-Octyloxyphenyl-5-(2-methyloctyl)-pyrimidine

2-p-Octyloxyphenyl-5-(3-methyloctyl)-pyrimidine

2-p-Octyloxyphenyl-5-(4-methyloctyl)-pyrimidine

2-p-Octyloxyphenyl-5-(5-methyloctyl)-pyrimidine

2-p-Octyloxyphenyl-5-(6-methyloctyl)-pyrimidine, m.p. 14° c.p. 44°

2-p-Octylphenyl-5-(2-methyloctyloxy)-pyrimidine

2-p-Octylphenyl-5-(3-methyloctyloxy)-pyrimidine

2-p-Octylphenyl-5-(4-methyloctyloxy)-pyrimidine

2-p-Octylphenyl-5-(5-methyloctyloxy)-pyrimidine

2-p-Octylphenyl-5-(6-methyloctyloxy)-pyrimidine m.p. 13°, c.p. 51°

2-p-(2-Methylbutoxy)-phenyl-5-butyloxypyrimidine

2-p-(2-Methylbutoxy)-phenyl-5-pentyloxypyrimidine

2-p-(2-Methylbutoxy)-phenyl-5-hexyloxypyrimidine

2-p-(2-Methylbutoxy)-phenyl-5-heptyloxypyrimidine

2-p-(2-Methylbutoxy)-phenyl-5-octyloxypyrimidine

2-p-(2-Methylbutoxy)-phenyl-5-nonyloxypyrimidine

2-p-(2-Methylbutoxy)-phenyl-5-decyloxypyrimidine

2-p-(2-Methylbutoxy)-phenyl-5-undecyloxypyrimidine, m.p. 58° c.p. 77°

2-p-(2-Methylbutoxy)-phenyl-5-dodecyloxypyrimidine

2-p-(2-Methylbutoxy)-phenyl-5-heptoxymethyloxypyrimidine

2-p-(2-Methylbutoxy)-phenyl-5-hexoxyethyloxypyrimidine

2-p-(2-Methylbutoxy)-phenyl-5-pentoxypropyloxypyrimidine

2-p-(3-Methylpentoxy)-phenyl-5-butyloxypyrimidine

2-p-(3-Methylpentoxy)-phenyl-5-pentyloxypyrimidine

2-p-(3-Methylpentoxy)-phenyl-5-hexyloxypyrimidine

2-p-(3-Methylpentoxy)-phenyl-5-heptyloxypyrimidine

2-p-(3-Methylpentoxy)-phenyl-5-octyloxypyrimidine, m.p. 52°, c.p. 76°

2-p-(3-Methylpentoxy)-phenyl-5-nonyloxypyrimidine

2-p-(3-Methylpentoxy)-phenyl-5-decyloxypyrimidine

2-p-(3-Methylpentoxy)-phenyl-5-undecyloxypyrimidine, m.p. 48° c.p. 76°

2-p-(3-Methylpentoxy)-phenyl-5-dodecyloxypyrimidine

2-p-(3-Methylpentoxy)-phenyl-5-heptoxymethyloxypyrimidine

2-p-(3-Methylpentoxy)-phenyl-5-hexoxyethyloxypyrimidine

2-p-(3-Methylpentoxy)-phenyl-5-pentoxypropyloxypyrimidine

2-p-(6-Methyloctoxy)-phenyl-5-butyloxypyrimidine

2-p-(6-Methyloctoxy)-phenyl-5-pentyloxypyrimidine

2-p-(6-Methyloctoxy)-phenyl-5-hexyloxypyrimidine

2-p-(6-Methyloctoxy)-phenyl-5-heptyloxypyrimidine

2-p-(6-Methyloctoxy)-phenyl-5-octyloxypyrimidine

2-p-(6-Methyloctoxy)-phenyl-5-nonyloxypyrimidine

2-p-(6-Methyloctoxy)-phenyl-5-decyloxypyrimidine

2-p-(6-Methyloctoxy)-phenyl-5-undecyloxypyrimidine, m.p. 41° c.p. 89°

2-p-(6-Methyloctoxy)-phenyl-5-dodecyloxypyrimidine

2-p-(6-Methyloctoxy)-phenyl-5-heptoxymethyloxypyrimidine

2-p-(6-Methyloctoxy)-phenyl-5-hexoxyethyloxypyrimidine

2-p-(6-Methyloctoxy)-phenyl-5-pentoxypropyloxypyrimidine

2-p-(2-Methyloctoxy)-phenyl-5-butyloxypyrimidine

2-p-(2-Methyloctoxy)-phenyl-5-pentyloxypyrimidine

2-p-(2-Methyloctoxy)-phenyl-5-hexyloxypyrimidine

2-p-(2-Methyloctoxy)-phenyl-5-heptyloxypyrimidine

2-p-(2-Methyloctoxy)-phenyl-5-octyloxypyrimidine, m.p. 36°, c.p. 62°,S_(C*) /S_(A*) 41°

2-p-(2-Methyloctoxy)-phenyl-5-nonyloxypyrimidine

2-p-(2-Methyloctoxy)-phenyl-5-decyloxypyrimidine

2-p-(2-Methyloctoxy)-phenyl-5-undecyloxypyrimidine

2-p-(2-Methyloctoxy)-phenyl-5-dodecyloxypyrimidine

2-p-(2-Methyloctoxy)-phenyl-5-heptoxymethyloxypyrimidine

2-p-(2-Methyloctoxy)-phenyl-5-hexoxyethyloxypyrimidine

2-p-(2-Methyloctoxy)-phenyl-5-pentoxypropyloxypyrimidine

2-p-(2-Methylbutyryloxy)-phenyl-5-butyloxypyrimidine

2-p-(2-Methylbutyryloxy)-phenyl-5-pentyloxypyrimidine

2-p-(2-Methylbutyryloxy)-phenyl-5-hexyloxypyrimidine

2-p-(2-Methylbutyryloxy)-phenyl-5-heptyloxypyrimidine

2-p-(2-Methylbutyryloxy)-phenyl-5-octyloxypyrimidine, m.p. 66°

2-p-(2-Methylbutyryloxy)-phenyl-5-nonyloxypyrimidine

2-p-(2-Methylbutyryloxy)-phenyl-5-decyloxypyrimidine

2-p-(2-Methylbutyryloxy)-phenyl-5-undecyloxypyrimidine, m.p. 43°, c.p.67°, S_(C*) /S_(A*) 64°

2-p-(2-Methylbutyryloxy)-phenyl-5-dodecyloxypyrimidine

2-p-(2-Methylbutyryloxy)-phenyl-5-heptoxymethyloxypyrimidine

2-p-(2-Methylbutyryloxy)-phenyl-5-hexoxyethyloxypyrimidine

2-p-(2-Methylbutyryloxy)-phenyl-5-pentoxypropyloxypyrimidine

2-p-(3-Methylpentanoyloxy)-phenyl-5-butyloxypyrimidine

2-p-(3-Methylpentanoyloxy)-phenyl-5-pentyloxypyrimidine

2-p-(3-Methylpentanoyloxy)-phenyl-5-hexyloxypyrimidine

2-p-(3-Methylpentanoyloxy)-phenyl-5-heptyloxypyrimidine

2-p-(3-Methylpentanoyloxy)-phenyl-5-octyloxypyrimidine, m.p. 70°, c.p.73°

2-p-(3-Methylpentanoyloxy)-phenyl-5-nonyloxypyrimidine

2-p-(3-Methylpentanoyloxy)-phenyl-5-decyloxypyrimidine

2-p-(3-Methylpentanoyloxy)-phenyl-5-undecyloxypyrimidine, m.p. 55°, c.p.78°

2-p-(3-Methylpentanoyloxy)-phenyl-5-dodecyloxypyrimidine

2-p-(3-Methylpentanoyloxy)-phenyl-5-heptoxymethyloxypyrimidine

2-p-(3-Methylpentanoyloxy)-phenyl-5-hexoxyethyloxypyrimidine

2-p-(3-Methylpentanoyloxy)-phenyl-5-pentoxypropyloxypyrimidine

2-p-(4-Methylhexanoyloxy)-phenyl-5-butyloxypyrimidine

2-p-(4-Methylhexanoyloxy)-phenyl-5-pentyloxypyrimidine

2-p-(4-Methylhexanoyloxy)-phenyl-5-hexyloxypyrimidine

2-p-(4-Methylhexanoyloxy)-phenyl-5-heptyloxypyrimidine

2-p-(4-Methylhexanoyloxy)-phenyl-5-octyloxypyrimidine, m.p. 78°

2-p-(4-Methylhexanoyloxy)-phenyl-5-nonyloxypyrimidine

2-p-(4-Methylhexanoyloxy)-phenyl-5-decyloxypyrimidine

2-p-(4-Methylhexanoyloxy)-phenyl-5-undecyloxypyrimidine

2-p-(4-Methylhexanoyloxy)-phenyl-5-dodecyloxypyrimidine

2-p-(4-Methylhexanoyloxy)-phenyl-5-heptoxymethyloxypyrimidine

2-p-(4-Methylhexanoyloxy)-phenyl-5-hexoxyethyloxypyrimidine

2-p-(4-Methylhexanoyloxy)-phenyl-5-pentoxypropyloxypyrimidine

2-p-(6-Methyloctanoyloxy)-phenyl-5-butyloxypyrimidine

2-p-(6-Methyloctanoyloxy)-phenyl-5-pentyloxypyrimidine

2-p-(6-Methyloctanoyloxy)-phenyl-5-hexyloxypyrimidine

2-p-(6-Methyloctanoyloxy)-phenyl-5-heptyloxypyrimidine

2-p-(6-Methyloctanoyloxy)-phenyl-5-octyloxypyrimidine, m.p. 76°, c.p.80°

2-p-(6-Methyloctanoyloxy)-phenyl-5-nonyloxypyrimidine

2-p-(6-Methyloctanoyloxy)-phenyl-5-decyloxypyrimidine

2-p-(6-Methyloctanoyloxy)-phenyl-5-undecyloxypyrimidine

2-p-(6-Methyloctanoyloxy)-phenyl-5-dodecyloxypyrimidine

2-p-(6-Methyloctanoyloxy)-phenyl-5-heptoxymethyloxypyrimidine

2-p-(6-Methyloctanoyloxy)-phenyl-5-hexoxyethyloxypyrimidine

2-p-(6-Methyloctanoyloxy)-phenyl-5-pentoxypropyloxypyrimidine

2-p-(6-Methyloctyloxy)-phenyl-5-butyloxycarbonylpyrimidine

2-p-(6-Methyloctyloxy)-phenyl-5-pentyloxycarbonylpyrimidine

2-p-(6-Methyloctyloxy)-phenyl-5-hexyloxycarbonylpyrimidine

2-p-(6-Methyloctyloxy)-phenyl-5-heptyloxycarbonylpyrimidine

2-p-(6-Methyloctyloxy)-phenyl-5-octyloxycarbonylpyrimidine, m.p. 78°,c.p. 80°

2-p-(6-Methyloctyloxy)-phenyl-5-nonyloxycarbonylpyrimidine

2-p-(6-Methyloctyloxy)-phenyl-5-decyloxycarbonylpyrimidine

2-p-(6-Methyloctyloxy)-phenyl-5-undecyloxycarbonylpyrimidine

2-p-(6-Methyloctyloxy)-phenyl-5-dodecyloxycarbonylpyrimidine

2-p-(6-Methyloctyloxy)-phenyl-5-heptoxymethyloxycarbonylpyrimidine

2-p-(6-Methyloctyloxy)-phenyl-5-hexoxyethyloxycarbonylpyrimidine

2-p-(6-Methyloctyloxy)-phenyl-5-pentoxypropyloxycarbonylpyrimidine

2-p-Octyloxyphenyl-5-(2-methyloctyloxycarbonyl)-pyrimidine

2-p-Octyloxyphenyl-5-(3-methyloctyloxycarbonyl)-pyrimidine

2-p-Octyloxyphenyl-5-(4-methyloctyloxycarbonyl)-pyrimidine

2-p-Octyloxyphenyl-5-(5-methyloctyloxycarbonyl)-pyrimidine

2-p-Octyloxyphenyl-5-(6-methyloctyloxycarbonyl)-pyrimidine, m.p. 80°

2-p-Dodecyloxyphenyl-5-(2-methyloctyloxycarbonyl)-pyrimidine

2-p-Undecyloxyphenyl-5-(2-methylbutoxy)-pyrimidine, m.p. 51°

2-p-Decyloxyphenyl-5-(2-methylbutoxy)-pyrimidine

2-p-Nonyloxyphenyl-5-(2-methylbutoxy)-pyrimidine

2-p-Octyloxyphenyl-5-(2-methylbutoxy)-pyrimidine

2-p-Heptyloxyphenyl-5-(2-methylbutoxy)-pyrimidine

2-p-Dodecanoyloxyphenyl-5-(2-methylbutoxy)-pyrimidine

2-p-Undecanoyloxyphenyl-5-(2-methylbutoxy)-pyrimidine, m.p. 58°

2-p-Decanoyloxyphenyl-5-(2-methylbutoxy)-pyrimidine

2-p-Nonanoyloxyphenyl-5-(2-methylbutoxy)-pyrimidine

2-p-Octanoyloxyphenyl-5-(2-methylbutoxy)-pyrimidine

2-p-Heptanoyloxyphenyl-5-(2-methylbutoxy)-pyrimidine

R-4-(5-Dodecylpyrimid-2-yl)-phenyl 2-chloropropionate

R-4-(5-Undecylpyrimid-2-yl)-phenyl 2-chloropropionate

R-4-(5-Decylpyrimid-2-yl)-phenyl-2 chloropropionate

R-4-(5-Octylpyrimid-2-yl)-phenyl-2 chloropropionate

R-4-(5-Heptylpyrimid-2-yl)-phenyl 2-chloropropionate, m.p. 93°

R-4-(5-Hexylpyrimid-2-yl)-phenyl 2-chloropropionate, m.p. 82°

R-4-(5-Pentylpyrimid-2-yl)-phenyl 2-chloropropionate

R-4-(5-Butylpyrimid-2-yl)-phenyl 2-chloropropionate

R-4-(5-Propylpyrimid-2-yl)-phenyl 2-chloropropionate.

Esterification of 5-(p-alkylphenyl)-pyrazin-2-ol (obtainable by SeO₂oxidation of p-alkylacetophenone, followed by reaction with glycinamidehydrochloride by methods known from the literature) gives rise in ananalogous manner to:

R-5-(p-Propylphenyl)-pyrazin-2-yl-2-chloropropionate

R-5-(p-Butylphenyl)-pyrazin-2-yl-2-chloropropionate

R-5-(p-Pentylphenyl)-pyrazin-2-yl-2-chloropropionate

R-5-(p-Hexylphenyl)-pyrazin-2-yl-2-chloropropionate

R-5-(p-Heptylphenyl)-pyrazin-2-yl-2-chloropropionate

R-5-(p-Octylphenyl)-pyrazin-2-yl-2-chloropropionate

R-5-(p-Nonylphenyl)-pyrazin-2-yl-2-chloropropionate

R-5-(p-Decylphenyl)-pyrazin-2-yl-2-chloropropionate

R-5-(p-Undecylphenyl)-pyrazin-2-yl-2-chloropropionate

R-5-(p-Dodecylphenyl)-pyrazin-2-yl-2-chloropropionate

The optically active alcohols or carboxylic acids used are either knownor they can be obtained, by analogy with known compounds, by methodsknown from the literature, for example by homologizing.

EXAMPLE 2

A suspension of 7.5 g of 4-(5-n-heptylpyrimidin-2-yl)-benzoic acid[obtainable by an alkaline saponification of2-(4-cyanophenyl)-5-n-heptylpyrimidine] in 80 ml of dichloromethane istreated with 3.3 g of d-2-octanol and 0.3 g of4-N,N-(dimethylamino)-pyridine; 5.8 g of dicyclohexylcarbodiimide isadded with stirring at 5°-10°, stirring is continued for 30 minutes at10° and subsequently overnight at room temperature, the mixture isfiltered off from the precipitated urea and is worked up in the usualmanner. 5-n-Heptyl-2-(4-carbo-d-2-octyloxyphenyl)-pyrimidine, m.p. 19°,is obtained.

The following are prepared in an analogous manner:

5-Dodecyl-2-(4-carbo-d-2-octyloxyphenyl)-pyrimidine

5-Undecyl-2-(4-carbo-d-2-octyloxyphenyl)-pyrimidine

5-Decyl-2-(4-carbo-d-2-octyloxyphenyl)-pyrimidine

5-Nonyl-2-(4-carbo-d-2-octyloxyphenyl)-pyrimidine, m.p. 15°

5-Octyl-2-(4-carbo-d-2-octyloxyphenyl)-pyrimidine

5-Hexyl-2-(4-carbo-d-2-octyloxyphenyl)-pyrimidine

5-Pentyl-2-(4-carbo-d-2-octyloxyphenyl)-pyrimidine

5-Butyl-2-(4-carbo-d-2-octyloxyphenyl)-pyrimidine

5-Propyl-2-(4-carbo-d-2-octyloxyphenyl)-pyrimidine

5-Ethyl-2-(4-carbo-d-2-octyloxyphenyl)-pyrimidine

5-Dodecyl-2-[4-carbo-(S-2-methyl-1-butoxy)-phenyl]-pyrimidine

5-Undecyl-2-[4-carbo-(S-2-methyl-1-butoxy)-phenyl]-pyrimidine

5-Decyl-2-[4-carbo-(S-2-methyl-1-butoxy)-phenyl]-pyrimidine

5-Nonyl-2-[4-carbo-(S-2-methyl-1-butoxy)-phenyl]-pyrimidine

5-Octyl-2-[4-carbo-(S-2-methyl-1-butoxy)-phenyl]-pyrimidine

5-Heptyl-2-[4-carbo-(S-2-methyl-1-butoxy)-phenyl]-pyrimidine, m.p. 55.5°

5-Hexyl-2-[4-carbo-(S-2-methyl-1-butoxy)-phenyl]-pyrimidine

5-Pentyl-2-[4-carbo-(S-2-methyl-1-butoxy)-phenyl]-pyrimidine

5-Butyl-2-[4-carbo-(S-2-methyl-1-butoxy)-phenyl]-pyrimidine

5-Propyl-2-[4-carbo-(S-2-methyl-1-butoxy)-phenyl]-pyrimidine

5-Ethyl-2-[4-carbo-(S-2-methyl-1-butoxy)-phenyl]-pyrimidine

R-(2-Chloropropyl)-p-(5-nonylpyrimidin-2-yl)-benzoate

R-(2-Chloropropyl)-p-(5-decylpyrimidin-2-yl)-benzoate

R-(2-Chloropropyl)-p-(5-undecylpyrimidin-2-yl)-benzoate

R-(2-Chloropropyl)-p-(5-dodecylpyrimidin-2-yl)-benzoate

R-(2-Chloropropyl)-p-(5-octylpyrimidin-2-yl)-benzoate

R-(2-Chloropropyl)-p-(5-heptylpyrimidin-2-yl)-benzoate

R-(2-Chloropropyl)-p-(5-hexylpyrimidin-2-yl)-benzoate

R-(2-Chloropropyl)-p-(5-pentylpyrimidin-2-yl)-benzoate

R-(2-Chloropropyl)-p-(5-butylpyrimidin-2-yl)-benzoate.

EXAMPLE 3

Esterification of 27.2 g of p-(5-n-hexylpyrimid-2-yl)-phenol withS-4-(2-methylbutyl)-benzoic acid in dichloromethane with the addition of25.0 g of dicyclohexylcarbodiimide gives rise, after the usual workingup, to S-4-(5-n-hexylpyrimid-2-yl)-phenyl 4-(2-methylbutyl)-benzoate.

The following are prepared in an analogous manner:

S-4-(5-Propylpyrimid-2-yl)phenyl 4-(2-methylbutyl)-benzoate

S-4-(5-Butylpyrimid-2-yl)phenyl 4-(2-methylbutyl)-benzoate

S-4-(5-Pentylpyrimid-2-yl)phenyl 4-(2-methylbutyl)-benzoate

S-4-(5-Heptylpyrimid-2-yl)phenyl 4-(2-methylbutyl)-benzoate

S-4-(5-Octylpyrimid-2-yl)phenyl 4-(2-methylbutyl)-benzoate

S-4-(5-Nonylpyrimid-2-yl)phenyl 4-(2-methylbutyl)-benzoate

S-4-(5-decylpyrimid-2-yl)phenyl 4-(2-methylbutyl)-benzoate

S-4-(5-Undecylpyrimid-2-yl)phenyl 4-(2-methylbutyl)-benzoate

S-4-(5-Dodecylpyrimid-2-yl)phenyl 4-(2-methylbutyl)-benzoate

4-(2-Methylbutyl)phenyl S-4-(5-propylpyrimid-2-yl)-benzoate

4-(2-Methylbutyl)phenyl S-4-(5-butylpyrimid-2-yl)-benzoate

4-(2-Methylbutyl)phenyl S-4-(5-pentylpyrimid-2-yl)-benzoate

4-(2-Methylbutyl)phenyl S-4-(5-hexylpyrimid-2-yl)-benzoate

4-(2-Methylbutyl)phenyl S-4-(5-heptylpyrimid-2-yl)-benzoate

4-(2-Methylbutyl)phenyl S-4-(5-octylpyrimid-2-yl)-benzoate

4-(2-Methylbutyl)phenyl S-4-(5-nonylpyrimid-2-yl)-benzoate

4-(2-Methylbutyl)phenyl S-4-(5-decylpyrimid-2-yl)-benzoate

4-(2-Methylbutyl)phenyl S-4-(5-undecylpyrimid-2-yl)-benzoate

4-(2-Methylbutyl)phenyl S-4-(5-dodecylpyrimid-2-yl)-benzoate

EXAMPLE 4

Esterification of 17.9 . . . (sic) of 5-n-butylpyrimidine-2-carboxylicacid with 16.4 g of S-4-(2-methylbutyl)phenol in di-chloromethane withthe addition of 25.0 g of dicyclohexyl-carbodiimide gives rise, afterthe usual working up, to S-4-(2-methylbutyl)phenyl5-butylpyrimidine-2-carboxylate.

The following were prepared in an analogous manner:

S-4-(2-Methylbutyl)phenyl 5-propylpyridine-2-carboxylate

S-4-(2-Methylbutyl)phenyl 5-pentylpyridine-2-carboxylate

S-4-(2-Methylbutyl)phenyl 5-hexylpyridine-2-carboxylate

S-4-(2-Methylbutyl)phenyl 5-heptylpyridine-2-carboxylate

S-4-(2-Methylbutyl)phenyl 5-octylpyridine-2-carboxylate

S-4-(2-Methylbutyl)phenyl 5-nonylpyridine-2-carboxylate

S-4-(2-Methylbutyl)phenyl 5-decylpyridine-2-carboxylate

S-4-(2-Methylbutyl)phenyl 5-undecylpyridine-2-carboxylate

S-4-(2-Methylbutyl)phenyl 5-dodecylpyridine-2-carboxylate

S-4-(2-Methylbutyl)phenyl 5-propylpyrimidine-2-carboxylate

S-4-(2-Methylbutyl)phenyl 5-pentylpyrimidine-2-carboxylate

S-4-(2-Methylbutyl)phenyl 5-hexylpyrimidine-2-carboxylate

S-4-(2-Methylbutyl)phenyl 5-heptylpyrimidine-2-carboxylate

S-4-(2-Methylbutyl)phenyl 5-octylpyrimidine-2-carboxylate

S-4-(2-Methylbutyl)phenyl 5-nonylpyrimidine-2-carboxylate

S-4-(2-Methylbutyl)phenyl 5-decylpyrimidine-2-carboxylate

S-4-(2-Methylbutyl)phenyl 5-undecylpyrimidine-2-carboxylate

S-4-(2-Methylbutyl)phenyl 5-dodecylpyrimidine-2-carboxylate.

EXAMPLE 5

In accordance with the procedure referred to in Example 3, 28.0 g of thecarboxylic acid obtainable from the known4-(5-n-hexylpyrazin-2-yl)-benzonitrile (Japanese Preliminary PublishedApplication 43,961/1983) by saponification with alcoholic potassiumhydroxide, followed by neutralization with dilute hydrochloric acid, aretreated with 25.0 g of dicyclohexylcarbodiimide and 13.0 g ofR-2-octanol. R-2-Octyl 4-(5-n-hexylpyrazin-2-yl)benzoate is obtainedafter the usual working up.

The following are prepared in an analogous manner:

R-2-Octyl 4-(5-propylpyrazin-2-yl)benzoate

R-2-Octyl 4-(5-butylpyrazin-2-yl)benzoate

R-2-Octyl 4-(5-pentylpyrazin-2-yl)benzoate

R-2-Octyl 4-(5-heptylpyrazin-2-yl)benzoate

R-2-Octyl 4-(5-octylpyrazin-2-yl)benzoate

R-2-Octyl 4-(5-nonylpyrazin-2-yl)benzoate

R-2-Octyl 4-(5-decylpyrazin-2-yl)benzoate

R-2-Octyl 4-(5-undecylpyrazin-2-yl)benzoate

R-2-Octyl 4-(5-dodecylpyrazin-2-yl)benzoate.

EXAMPLE 6

The solution prepared according to Grignard from 2.4 g of magnesium,15.1 g of S-2-methylbutyl bromide and 200 ml of THF is treated with asolution of 26.1 g of 4-(5-n-hexylpyrazin-2-yl)-benzonitrile. Theresidue remaining from the organic phase after the solvent has beendistilled off, is worked up in the usual manner. The optically active3-methylvaleryl-4-(5-n-hexylpyrazin-2-yl)benzene is obtained.

The following are prepared in an analogous manner:

3-Methylvaleryl-4-(5-n-propylpyrazin-2-yl)-benzene

3-Methylvaleryl-4-(5-n-butylpyrazin-2-yl)-benzene

3-Methylvaleryl-4-(5-n-pentylpyrazin-2-yl)-benzene

3-Methylvaleryl-4-(5-n-heptylpyrazin-2-yl)-benzene

3-Methylvaleryl-4-(5-n-octylpyrazin-2-yl)-benzene

3-Methylvaleryl-4-(5-n-nonylpyrazin-2-yl)-benzene

3-Methylvaleryl-4-(5-n-decylpyrazin-2-yl)-benzene

3-Methylvaleryl-4-(5-n-undecylpyrazin-2-yl)-benzene

3-Methylvaleryl-4-(5-n-dodecylpyrazin-2-yl)-benzene

EXAMPLE 7

A liquid crystalline phase consisting of

38.3% of 2-p-Nonyloxyphenyl-5-nonylpyrimidine,

2.0% of 2-p-Hexyloxyphenyl-5-nonylpyrimidine,

36.1% of 2-p-Decyloxyphenyl-5-heptylpyrimidine,

5.9% of 2-p-Nonyloxyphenyl-5-heptylpyrimidine,

5.9% of 2-p-Octyloxyphenyl-5-heptylpyrimidine,

5.9% of 2-p-Heptyloxyphenyl-5-heptylpyrimidine, and

5.9% of 2-p-Hexyloxyphenyl-5-heptylpyrimidine

is doped with various amounts of the chiral compoundR-4-(5-hexylpyrimid-2-yl)phenyl 2-chloropropionate. The phase transitiontemperatures as well as the values of the spontaneous polarization ofthe resultant mixtures are given in the table below:

    ______________________________________                                        Addition of X% of the chiral dopant                                           X       S.sub.C *       S.sub.A *                                                                          Ch     I    P                                    ______________________________________                                        3              48.1          65     68.7 1.08                                 6              41.0          64.1   68.1 2.14                                 10             34.5          63     68   3.12                                 ______________________________________                                    

EXAMPLE 8

A mixture of 23.6 g of p-(5-n-heptylpyrimidin-2-yl)cinnamic acid (m.p.201°, obtainable by boiling for 48 hours a mixture of 22.2 g of2-p-bromophenyl-5-n-heptylpyrimidine, 18.4 g of triethylamine, 9.2 g ofacrylic acid, 0.17 g of Pd(II) acetate, 0.6 g of tritolylphosphine and75 ml of acetonitrile, followed by cooling to 0°, filtering off withsuction, washing of the precipitate with acetonitrile and water andrecrystallization from toluene), 13.0 g of R-2-octanol and 25.0 g ofdicyclohexylcarbodiimide in THF is boiled for 24 hours in the presenceof dimethylaminopyridine and worked up in the usual manner. 2-OctylR-p-(5-n-heptylpyrimidin-2-yl)cinnamate, m.p. 40°, c.p. 58°, isobtained.

The following are prepared in an analogous manner:

2-Octyl R-p-(5-propylpyrimidin-2-yl)cinnamate

2-Octyl R-p-(5-butylpyrimidin-2-yl)cinnamate

2-Octyl R-p-(5-pentylpyrimidin-2-yl)cinnamate

2-Octyl R-p-(5-hexylpyrimidin-2-yl)cinnamate

2-Octyl R-p-(5-octylpyrimidin-2-yl)cinnamate

2-Octyl R-p-(5-nonylpyrimidin-2-yl)cinnamate

2-Octyl R-p-(5-decylpyrimidin-2-yl)cinnamate

2-Octyl R-p-(5-undecylpyrimidin-2-yl)cinnamate

2-Octyl R-p-(5-dodecylpyrimidin-2-yl)cinnamate

2-Methylbutyl R-p-(5-propylpyrimidin-2-yl)cinnamate

2-Methylbutyl R-p-(5-butylpyrimidin-2-yl)cinnamate

2-Methylbutyl R-p-(5-pentylpyrimidin-2-yl)cinnamate

2-Methylbutyl R-p-(5-hexylpyrimidin-2-yl)cinnamate

2-Methylbutyl R-p-(5-heptylpyrimidin-2-yl)cinnamate m.p. 58°, c.p. 96°

2-Methylbutyl R-p-(5-octylpyrimidin-2-yl)cinnamate

2-Methylbutyl R-p-(5-nonylpyrimidin-2-yl)cinnamate

2-Methylbutyl R-p-(5-decylpyrimidin-2-yl)cinnamate

2-Methylbutyl R-p-(5-undecylpyrimidin-2-yl)cinnamate

2-Methylbutyl R-p-(5-dodecylpyrimidin-2-yl)cinnamate

EXAMPLE 9

26.3 g of (S)-3-chlorobutyl-1-tosylate, preparable fromp-toluenesulfonyl chloride and (S)-3-chlorobutan-1-ol, and 27.2 g of4-(5-n-hexylpyrimidin-2-yl)phenol are added to a suspension of 40 g ofpotassium carbonate in 200 ml of acetone. After 24 hours, boiling underreflux, the reaction mixture is filtered, the filtrate is freed fromsolvent and the residue is twice recrystallized from ethanol.(S)-2-[p-(3-Chlorobutyloxy)phenyl]-5-n-hexyl-pyrimidine is obtained.

The following are obtained in an analogous manner:

2-[p-(3-Chlorobutyloxy)-phenyl]-5-n-butylpyrimidine

2-[p-(3-Chlorobutyloxy)-phenyl]-5-n-pentylpyrimidine

2-[p-(3-Chlorobutyloxy)-phenyl]-5-n-heptylpyrimidine

2-[p-(3-Chlorobutyloxy)-phenyl]-5-n-octylpyrimidine

2-[p-(3-Chlorobutyloxy)-phenyl]-5-n-nonylpyrimidine

2-[p-(3-Chlorobutyloxy)-phenyl]-5-n-decylpyrimidine

2-[p-(3-Chlorobutyloxy)-phenyl]-5-n-undecylpyrimidine

2-[p-(3-Chlorobutyloxy)-phenyl]-5-n-dodecylpyrimidine

2-[p-(3-Cyanobutyloxy)-phenyl]-5-n-butylpyrimidine

2-[p-(3-Cyanobutyloxy)-phenyl]-5-n-pentylpyrimidine

2-[p-(3-Cyanobutyloxy)-phenyl]-5-n-hexylpyrimidine

2-[p-(3-Cyanobutyloxy)-phenyl]-5-n-heptylpyrimidine

2-[p-(3-Cyanobutyloxy)-phenyl]-5-n-octylpyrimidine

2-[p-(3-Cyanobutyloxy)-phenyl]-5-n-nonylpyrimidine

2-[p-(3-Cyanobutyloxy)-phenyl]-5-n-decylpyrimidine

2-[p-(3-Cyanobutyloxy)-phenyl]-5-n-undecylpyrimidine

2-[p-(3-Cyanobutyloxy)-phenyl]-5-n-dodecylpyrimidine

EXAMPLE 10

A mixture of 40 g of(S)-4,6-dichloro-2-(p-heptyloxyphenyl)-5-(2-methylbutyl)-pyrimidine[obtainable by reacting (S)-2-methylbutyl bromide with diethyl malonatein the presence of sodium methanolate, followed by condensation of theresultant diethyl (S)-2-methylbutyl malonate with p-heptyloxybenzamidinehydrochloride, and reacting the resultant(S)-4,6-dihydroxy-2-(p-heptyloxyphenyl)-5-(2-methylbutyl)-pyrimidinewith phosphoroxy trichloride and dimethylaniline], 400 ml of methanol,40 ml of triethylamine and 20 g of Pd-C (5%) is hydrogenated at roomtemperature under normal pressure until the theoretical amount ofhydrogen has been taken up. After filtering off the catalyst anddistilling off the solvent, the residue is recrystallized from ethanol.(S)-2-(p-Heptyloxyphenyl)-5-(2-methylbutyl)-pyrimidine is obtained.

The following are prepared in an analogous manner:

2-(p-Pentyloxyphenyl)-5-(2-methylbutyl)-pyrimidine

2-(p-Hexyloxyphenyl)-5-(2-methylbutyl)-pyrimidine

2-(p-Octyloxyphenyl)-5-(2-methylbutyl)-pyrimidine

2-(p-Nonyloxyphenyl)-5-(2-methylbutyl)-pyrimidine

2-(p-Decyloxyphenyl)-5-(2-methylbutyl)-pyrimidine

2-(p-Undecyloxyphenyl)-5-(2-methylbutyl)-pyrimidine

2-(p-Dodecyloxyphenyl)-5-(2-methylbutyl)-pyrimidine

EXAMPLE 11

A mixture of 8 g of (S,S)-3-methyl-2-chloropentanoic acid, 16 g ofp-(5-n-octylpyrimidin-2-yl)phenol, 11.6 g ofN,N-dicyclohexylcarbodiimide, 0.6 g of 4-N,N-dimethylamino-pyridine and300 ml of dichloromethane is stirred overnight at room temperature.After filtering off the precipitated urea derivative, the filtrate iswashed with dilute hydrochloric acid and water, and the organic phase isworked up in the usual manner. p-(5-n-Octylpyrimidin-2-yl)-phenyl(S,S)-3-methyl-2-chloropentanoate is obtained.

The following are prepared in an analogous manner:

p-(5-Pentylpyrimidin-2-yl)phenyl 3-methyl-2-chloropentanoate

p-(5-Hexylpyrimidin-2-yl)phenyl 3-methyl-2-chloropentanoate

p-(5-Heptylpyrimidin-2-yl)phenyl 3-methyl-2-chloropentanoate

p-(5-Nonylpyrimidin-2-yl)phenyl 3-methyl-2-chloropentanoate

p-(5-Decylpyrimidin-2-yl)phenyl 3-methyl-2-chloropentanoate

p-(5-Pentylpyrimidin-2-yl)phenyl 3-methyl-2-bromopentanoate

p-(5-Hexylpyrimidin-2-yl)phenyl 3-methyl-2-bromopentanoate

p-(5-Heptylpyrimidin-2-yl)phenyl 3-methyl-2-bromopentanoate

p-(5-Octylpyrimidin-2-yl)phenyl 3-methyl-2-bromopentanoate

p-(5-Nonylpyrimidin-2-yl)phenyl 3-methyl-2-bromopentanoate

p-(5-Decylpyrimidin-2-yl)phenyl 3-methyl-2-bromopentanoate

p-(5-Pentylpyrazin-2-yl)phenyl 3-methyl-2-chloropentanoate

p-(5-Hexylpyrazin-2-yl)phenyl 3-methyl-2-chloropentanoate

p-(5-Heptylpyrazin-2-yl)phenyl 3-methyl-2-chloropentanoate

p-(5-Octylpyrazin-2-yl)phenyl 3-methyl-2-chloropentanoate

p-(5-Nonylpyrazin-2-yl)phenyl 3-methyl-2-chloropentanoate

p-(5-Decylpyrazin-2-yl)phenyl 3-methyl-2-chloropentanoate

p-(5-Pentylpyrazin-2-yl)phenyl 3-methyl-2-cyanopentanoate

p-(5-Hexylpyrazin-2-yl)phenyl 3-methyl-2-cyanopentanoate

p-(5-Heptylpyrazin-2-yl)phenyl 3-methyl-2-cyanopentanoate

p-(5-Octylpyrazin-2-yl)phenyl 3-methyl-2-cyanopentanoate

p-(5-Nonylpyrazin-2-yl)phenyl 3-methyl-2-cyanopentanoate

p-(5-Decylpyrazin-2-yl)phenyl 3-methyl-2-cyanopentanoate

p-(5-Pentylpyrimidin-2-yl)phenyl 3-methyl-2-chlorohexanecarboxylate

p-(5-Hexylpyrimidin-2-yl)phenyl 3-methyl-2-chlorohexanecarboxylate

p-(5-Heptylpyrimidin-2-yl)phenyl 3-methyl-2-chlorohexanecarboxylate

p-(5-Octylpyrimidin-2-yl)phenyl 3-methyl-2-chlorohexanecarboxylate

p-(5-Nonylpyrimidin-2-yl)phenyl 3-methyl-2-chlorohexanecarboxylate

p-(5-Decylpyrimidin-2-yl)phenyl 3-methyl-2-chlorohexanecarboxylate

p-(5-Pentylpyrimidin-2-yl)phenyl 3-methyl-2-cyanohexanecarboxylate

p-(5-Hexylpyrimidin-2-yl)phenyl 3-methyl-2-cyanohexanecarboxylate

p-(5-Heptylpyrimidin-2-yl)phenyl 3-methyl-2-cyanohexanecarboxylate

p-(5-Octylpyrimidin-2-yl)phenyl 3-methyl-2-cyanohexanecarboxylate

p-(5-Nonylpyrimidin-2-yl)phenyl 3-methyl-2-cyanohexanecarboxylate

p-(5-Decylpyrimidin-2-yl)phenyl 3-methyl-2-cyanohexanecarboxylate

p-(5-Pentylpyrimidin-2-yl)phenyl 3-chloro-2-methylpentanoate

p-(5-Hexylpyrimidin-2-yl)phenyl 3-chloro-2-methylpentanoate

p-(5-Heptylpyrimidin-2-yl)phenyl 3-chloro-2-methylpentanoate

p-(5-Octylpyrimidin-2-yl)phenyl 3-chloro-2-methylpentanoate

p-(5-Nonylpyrimidin-2-yl)phenyl 3-chloro-2-methylpentanoate

p-(5-Decylpyrimidin-2-yl)phenyl 3-chloro-2-methylpentanoate

p-(5-Pentylpyrazin-2-yl)phenyl 3-bromo-2-methylpentanoate

p-(5-Hexylpyrazin-2-yl)phenyl 3-bromo-2-methylpentanoate

p-(5-Heptylpyrazin-2-yl)phenyl 3-bromo-2-methylpentanoate

p-(5-Octylpyrazin-2-yl)phenyl 3-bromo-2-methylpentanoate

p-(5-nonylpyrazin-2-yl)phenyl 3-bromo-2-methylpentanoate

p-(5-Decylpyrazin-2-yl)phenyl 3-bromo-2-methylpentanoate

p-(5-Pentylpyrimidin-2-yl)phenyl 3-cyano-2-methylhexanoate

p-(5-Hexylpyrimidin-2-yl)phenyl 3-cyano-2-methylhexanoate

p-(5-Heptylpyrimidin-2-yl)phenyl 3-cyano-2-methylhexanoate

p-(5-Octylpyrimidin-2-yl)phenyl 3-cyano-2-methylhexanoate

p-(5-Nonylpyrimidin-2-yl)phenyl 3-cyano-2-methylhexanoate

p-(5-Decylpyrimidin-2-yl)phenyl 3-cyano-2-methylhexanoate.

EXAMPLE 12

0.01 mol of optically active1-[4-(5-heptylpyrimidin-2-yl)phenyl-1]propan-2-ol (prepared fromcommercial R-propylene oxide and4-(5-heptylpyrimidin-2-yl)phenylmagnesium bromide) is stirred togetherwith 0.01 mol of butyric acid, 2.3 g of dicyclohexylcarbodiimide, 0.2 gof 4-N,N-dimethylaminopyridine and 25 ml of dichloromethane at roomtemperature for 48 hours.

The mixture is then cooled in an icebath, and the precipitate ofdicylcohexylurea is filtered off with suction and washed withdichloromethane. The combined filtrates are evaporated andchromatographed over silica gel. After recrystallization, opticallyactive 1-[4-(5-heptylpyrimidin-2-yl)-phenyl]-2-propyl butyrate isobtained.

The following are prepared in an analogous manner:

1-[4-(5-Propylpyrimidin-(2)-yl)phenyl]-2-propyl butyrate

1-[4-(5-Butylpyrimidin-(2)-yl)phenyl]-2-propyl butyrate

1-[4-(5-Pentylpyrimidin-(2)-yl)phenyl]-2-propyl butyrate

1-[4-(5-Hexylpyrimidin-(2)-yl)phenyl]-2-propyl butyrate

1-[4-(5-Octylpyrimidin-(2)-yl)phenyl]-2-propyl butyrate

1-[4-(5-Nonylpyrimidin-(2)-yl)phenyl]-2-propyl butyrate

1-[4-(5-Propyloxypyrimidin-(2)-yl)phenyl]-2-propyl butyrate

1-[4-(5-Butyloxypyrimidin-(2)-yl)phenyl]-2-propyl butyrate

1-[4-(5-Pentyloxypyrimidin-(2)-yl)phenyl]-2-propyl butyrate

1-[4-(5-Hexyloxypyrimidin-(2)-yl)phenyl]-2-propyl butyrate

1-[4-(5-Heptyloxypyrimidin-(2)-yl)phenyl]-2-propyl butyrate

1-[4-(5-Octyloxypyrimidin-(2)-yl)phenyl]-2-propyl butyrate

1-[4-(5-Nonyloxypyrimidin-(2)-yl)phenyl]-2-propyl butyrate

1-[4-(5-Propylpyrimidin-(2)-yl)phenyl]-2-propyl propionate

1-[4-(5-Butylpyrimidin-(2)-yl)phenyl]-2-propyl propionate

1-[4-(5-Pentylpyrimidin-(2)-yl)phenyl]-2-propyl propionate

1-[4-(5-Hexylpyrimidin-(2)-yl)phenyl]-2-propyl propionate

1-[4-(5-Heptylpyrimidin-(2)-yl)phenyl]-2-propyl propionate

1-[4-(5-Octylpyrimidin-(2)-yl)phenyl]-2-propyl propionate

1-[4-(5-Nonylpyrimidin-(2)-yl)phenyl]-2-propyl propionate

1-[4-(5-Propyloxypyrimidin-(2)-yl)phenyl]-2-propyl propionate

1-[4-(5-Butyloxypyrimidin-(2)-yl)phenyl]-2-propyl propionate

1-[4-(5-Pentyloxypyrimidin-(2)-yl)phenyl]-2-propyl propionate

1-[4-(5-Hexyloxypyrimidin-(2)-yl)phenyl]-2-propyl propionate

1-[4-(5-Heptyloxypyrimidin-(2)-yl)phenyl]-2-propyl propionate

1-[4-(5-Octyloxypyrimidin-(2)-yl)phenyl]-2-propyl propionate

1-[4-(5-Nonyloxypyrimidin-(2)-yl)phenyl]-2-propyl propionate

1-[4-(5-Propylpyrimidin-(2)-yl)phenyl]-2-propyl valerate

1-[4-(5-Butylpyrimidin-(2)-yl)phenyl]-2-propyl valerate

1-[4-(5-Pentylpyrimidin-(2)-yl)phenyl]-2-propyl valerate

1-[4-(5-Hexylpyrimidin-(2)-yl)phenyl]-2-propyl valerate

1-[4-(5-Heptylpyrimidin-(2)-yl)phenyl]-2-propyl valerate

1-[4-(5-Octylpyrimidin-(2)-yl)phenyl]-2-propyl valerate

1-[4-(5-Nonylpyrimidin-(2)-yl)phenyl]-2-propyl valerate

1-[4-(5-Propyloxypyrimidin-(2)-yl)phenyl]-2-propyl valerate

1-[4-(5-Butyloxypyrimidin-(2)-yl)phenyl]-2-propyl valerate

1-[4-(5-Pentyloxypyrimidin-(2)-yl)phenyl]-2-propyl valerate

1-[4-(5-Hexyloxypyrimidin-(2)-yl)phenyl]-2-propyl valerate

1-[4-(5-Heptyloxypyrimidin-(2)-yl)phenyl]-2-propyl valerate

1-[4-(5-Octyloxypyrimidin-(2)-yl)phenyl]-2-propyl valerate

1-[4-(5-Nonyloxypyrimidin-(2)-yl)phenyl]-2-propyl valerate

1-[4-(5-Propylpyrimidin-(2)-yl)phenyl]-2-propyl acetate

1-[4-(5-Butylpyrimidin-(2)-yl)phenyl]-2-propyl acetate

1-[4-(5-Pentylpyrimidin-(2)-yl)phenyl]-2-propyl acetate

1-[4-(5-Hexylpyrimidin-(2)-yl)phenyl]-2-propyl acetate

1-[4-(5-Heptylpyrimidin-(2)-yl)phenyl]-2-propyl acetate

1-[4-(5-Octylpyrimidin-(2)-yl)phenyl]-2-propyl acetate

1-[4-(5-Nonylpyrimidin-(2)-yl)phenyl]-2-propyl acetate

1-[4-(5-Propyloxypyrimidin-(2)-yl)phenyl]-2-propyl acetate

1-[4-(5-Butyloxypyrimidin-(2)-yl)phenyl]-2-propyl acetate

1-[4-(5-Pentyloxypyrimidin-(2)-yl)phenyl]-2-propyl acetate

1-[4-(5-Hexyloxypyrimidin-(2)-yl)phenyl]-2-propyl acetate

1-[4-(5-Heptyloxypyrimidin-(2)-yl)phenyl]-2-propyl acetate

1-[4-(5-Octyloxypyrimidin-(2)-yl)phenyl]-2-propyl acetate

1-[4-(5-Nonyloxypyrimidin-(2)-yl)phenyl]-2-propyl acetate

1-[4-(5-Propylphenyl)pyrazin-(2)-yl]-2-propyl acetate

1-[4-(5-Butylphenyl)pyrazin-(2)-yl]-2-propyl acetate

1-[4-(5-Pentylphenyl)pyrazin-(2)-yl]-2-propyl acetate

1-[4-(5-Hexylphenyl)pyrazin-(2)-yl]-2-propyl acetate

1-[4-(5-Heptylphenyl)pyrazin-(2)-yl]-2-propyl acetate

1-[4-(5-Octylphenyl)pyrazin-(2)-yl]-2-propyl acetate

1-[4-(5-Nonylphenyl)pyrazin-(2)-yl]-2-propyl acetate

1-[4-(5-Propyloxyphenyl)pyrazin-(2)-yl]-2-propyl acetate

1-[4-(5-Butyloxyphenyl)pyrazin-(2)-yl]-2-propyl acetate

1-[4-(5-Pentyloxyphenyl)pyrazin-(2)-yl]-2-propyl acetate

1-[4-(5-Hexyloxyphenyl)pyrazin-(2)-yl]-2-propyl acetate

1-[4-(5-Heptyloxyphenyl)pyrazin-(2)-yl]-2-propyl acetate

1-[4-(5-Octyloxyphenyl)pyrazin-(2)-yl]-2-propyl acetate

1-[4-(5-Nonyloxyphenyl)pyrazin-(2)-yl]-2-propyl acetate

1-[4-(5-Propylphenyl)pyrazin-(2)-yl]-2-propyl propionate

1-[4-(5-Butylphenyl)pyrazin-(2)-yl]-2-propyl propionate

1-[4-(5-Pentylphenyl)pyrazin-(2)-yl]-2-propyl propionate

1-[4-(5-Hexylphenyl)pyrazin-(2)-yl]-2-propyl propionate

1-[4-(5-Heptylphenyl)pyrazin-(2)-yl]-2-propyl propionate

1-[4-(5-Octylphenyl)pyrazin-(2)-yl]-2-propyl propionate

1-[4-(5-Nonylphenyl)pyrazin-(2)-yl]-2-propyl propionate

1-[4-(5-Propyloxyphenyl)pyrazin-(2)-yl]-2-propyl propionate

1-[4-(5-Butyloxyphenyl)pyrazin-(2)-yl]-2-propyl propionate

1-[4-(5-Pentyloxyphenyl)pyrazin-(2)-yl]-2-propyl propionate

1-[4-(5-Hexyloxyphenyl)pyrazin-(2)-yl]-2-propyl propionate

1-[4-(5-Heptyloxyphenyl)pyrazin-(2)-yl]-2-propyl propionate

1-[4-(5-Octyloxyphenyl)pyrazin-(2)-yl]-2-propyl propionate

1-[4-(5-Nonyloxyphenyl)pyrazin-(2)-yl]-2-propyl propionate

1-[4-(5-Propylphenyl)pyrazin-(2)-yl]-2-propyl butyrate

1-[4-(5-Butylphenyl)pyrazin-(2)-yl]-2-propyl butyrate

1-[4-(5-Pentylphenyl)pyrazin-(2)-yl]-2-propyl butyrate

1-[4-(5-Hexylphenyl)pyrazin-(2)-yl]-2-propyl butyrate

1-[4-(5-Heptylphenyl)pyrazin-(2)-yl]-2-propyl butyrate

1-[4-(5-Octylphenyl)pyrazin-(2)-yl]-2-propyl butyrate

1-[4-(5-Nonylphenyl)pyrazin-(2)-yl]-2-propyl butyrate

1-[4-(5-Propyloxyphenyl)pyrazin-(2)-yl]-2-propyl butyrate

1-[4-(5-Butyloxyphenyl)pyrazin-(2)-yl]-2-propyl butyrate

1-[4-(5-Pentyloxyphenyl)pyrazin-(2)-yl]-2-propyl butyrate

1-[4-(5-Hexyloxyphenyl)pyrazin-(2)-yl]-2-propyl butyrate

1-[4-(5-Heptyloxyphenyl)pyrazin-(2)-yl]-2-propyl butyrate

1-[4-(5-Octyloxyphenyl)pyrazin-(2)-yl]-2-propyl butyrate

1-[4-(5-Nonyloxyphenyl)pyrazin-(2)-yl]-2-propyl butyrate

1-[4-(5-Propylphenyl)pyrazin-(2)-yl]-2-propyl valerate

1-[4-(5-Butylphenyl)pyrazin-(2)-yl]-2-propyl valerate

1-[4-(5-Pentylphenyl)pyrazin-(2)-yl]-2-propyl valerate

1-[4-(5-Hexylphenyl)pyrazin-(2)-yl]-2-propyl valerate

1-[4-(5-Heptylphenyl)pyrazin-(2)-yl]-2-propyl valerate

1-[4-(5-Octylphenyl)pyrazin-(2)-yl]-2-propyl valerate

1-[4-(5-Nonylphenyl)pyrazin-(2)-yl]-2-propyl valerate

1-[4-(5-Propyloxyphenyl)pyrazin-(2)-yl]-2-propyl valerate

1-[4-(5-Butyloxyphenyl)pyrazin-(2)-yl]-2-propyl valerate

1-[4-(5-Pentyloxyphenyl)pyrazin-(2)-yl]-2-propyl valerate

1-[4-(5-Hexyloxyphenyl)pyrazin-(2)-yl]-2-propyl valerate

1-[4-(5-Heptyloxyphenyl)pyrazin-(2)-yl]-2-propyl valerate

1-[4-(5-Octyloxyphenyl)pyrazin-(2)-yl]-2-propyl valerate

1-[4-(5-Nonyloxyphenyl)pyrazin-(2)-yl]-2-propyl valerate

EXAMPLE 13

0.01 mol of dextrorotatory 3-[4-(5-heptylpyrimidin-(2)-yl)phenyl]butyricacid, obtained by hydrogenation of the corresponding 2-butenoic acidover 5% Pd/carbon in tetrahydrofuran and racemic splitting with(+)-ephedrine (2-methylamino-1-phenylpropan-1-ol), α_(D) ²⁰ =+3.3°, isesterified with 0.01 mol of optically active 2-octanol in a manneranalogous to that of Example 12. After purification by chromatographyand recrystallization, 2-octyl3-[4-(5-heptylpyrimidin-(2)-yl)phenyl]butyrate is obtained.

The following are prepared in an analogous manner:

2-Octyl 3-[4-(5-propylpyrimidin-(2)-yl)phenyl]butyrate

2-Octyl 3-[4-(5-butylpyrimidin-(2)-yl)phenyl]butyrate

2-Octyl 3-[4-(5-pentylpyrimidin-(2)-yl)phenyl]butyrate

2-Octyl 3-[4-(5-hexylpyrimidin-(2)-yl)phenyl]butyrate

2-Octyl 3-[4-(5-octylpyrimidin-(2)-yl)phenyl]butyrate

2-Octyl 3-[4-(5-nonylpyrimidin-(2)-yl)phenyl]butyrate

2-Octyl 3-[4-(5-propyloxypyrimidin-(2)-yl)phenyl]butyrate

2-Octyl 3-[4-(5-butyloxypyrimidin-(2)-yl)phenyl]butyrate

2-Octyl 3-[4-(5-pentyloxypyrimidin-(2)-yl)phenyl]butyrate

2-Octyl 3-[4-(5-hexyloxypyrimidin-(2)-yl)phenyl]butyrate

2-Octyl 3-[4-(5-heptyloxypyrimidin-(2)-yl)phenyl]butyrate

2-Octyl 3-[4-(5-octyloxypyrimidin-(2)-yl)phenyl]butyrate

2-Octyl 3-[4-(5-nonyloxypyrimidin-(2)-yl)phenyl]butyrate

Hexyl 3-[4-(5-propylpyrimidin-(2)-yl)phenyl]butyrate

Hexyl 3-[4-(5-butylpyrimidin-(2)-yl)phenyl]butyrate

Hexyl 3-[4-(5-pentylpyrimidin-(2)-yl)phenyl]butyrate

Hexyl 3-[4-(5-hexylpyrimidin-(2)-yl)phenyl]butyrate

Hexyl 3-[4-(5-heptylpyrimidin-(2)-yl)phenyl]butyrate

Hexyl 3-[4-(5-octylpyrimidin-(2)-yl)phenyl]butyrate

Hexyl 3-[4-(5-nonylpyrimidin-(2)-yl)phenyl]butyrate

Hexyl 3-[4-(5-propyloxypyrimidin-(2)-yl)phenyl]butyrate

Hexyl 3-[4-(5-butyloxypyrimidin-(2)-yl)phenyl]butyrate

Hexyl 3-[4-(5-pentyloxypyrimidin-(2)-yl)phenyl]butyrate

Hexyl 3-[4-(5-hexyloxypyrimidin-(2)-yl)phenyl]butyrate

Hexyl 3-[4-(5-heptyloxypyrimidin-(2)-yl)phenyl]butyrate

Hexyl 3-[4-(5-octyloxypyrimidin-(2)-yl)phenyl]butyrate

Hexyl 3-[4-(5-nonyloxypyrimidin-(2)-yl)phenyl]butyrate

2-Methylbutyl 3-[4-(5-propylpyrimidin-(2)-yl)phenyl]butyrate

2-Methylbutyl 3-[4-(5-butylpyrimidin-(2)-yl)phenyl]butyrate

2-Methylbutyl 3-[4-(5-pentylpyrimidin-(2)-yl)phenyl]butyrate

2-Methylbutyl 3-[4-(5-hexylpyrimidin-(2)-yl)phenyl]butyrate

2-Methylbutyl 3-[4-(5-heptylpyrimidin-(2)-yl)phenyl]butyrate

2-Methylbutyl 3-[4-(5-octylpyrimidin-(2)-yl)phenyl]butyrate

2-Methylbutyl 3-[4-(5-nonylpyrimidin-(2)-yl)phenyl]butyrate

2-Methylbutyl 3-[4-(5-propyloxypyrimidin-(2)-yl)phenyl]butyrate

2-Methylbutyl 3-[4-(5-butyloxypyrimidin-(2)-yl)phenyl]butyrate

2-Methylbutyl 3-[4-(5-pentyloxypyrimidin-(2)-yl)phenyl]butyrate

2-Methylbutyl 3-[4-(5-hexyloxypyrimidin-(2)-yl)phenyl]butyrate

2-Methylbutyl 3-[4-(5-heptyloxypyrimidin-(2)-yl)phenyl]butyrate

2-Methylbutyl 3-[4-(5-octyloxypyrimidin-(2)-yl)phenyl]butyrate

2-Methylbutyl 3-[4-(5-nonyloxypyrimidin-(2)-yl)phenyl]butyrate.

EXAMPLE 14

0.01 mol of 4-(5-hexylpyrimidin-(2)-yl)phenyl α-chloropropionate(Example 1) is heated with 0.01 mol of sodium heptanolate in 20 ml ofN-methylpyrrolidone for 2 hours at 80°. The mixture is then poured ontowater and is extracted with toluene and the extract evaporated. Afterpurification by chromatography and recrystallization,4-(5-hexylpyrimidin-(2)-yl)phenyl α-heptyloxypropionate is obtained.

The following are prepared in an analogous manner:

4-(5-Propylpyrimidin-(2)-yl)phenyl α-heptyloxypropionate

4-(5-Butylpyrimidin-(2)-yl)phenyl α-heptyloxypropionate

4-(5-Pentylpyrimidin-(2)-yl)phenyl α-heptyloxypropionate

4-(5-Heptylpyrimidin-(2)-yl)phenyl α-heptyloxypropionate

4-(5-Octylpyrimidin-(2)-yl)phenyl α-heptyloxypropionate

4-(5-Nonylpyrimidin-(2)-yl)phenyl α-heptyloxypropionate

4-(5-Propyloxypyrimidin-(2)-yl)phenyl α-heptyloxypropionate

4-(5-Butyloxypyrimidin-(2)-yl)phenyl α-heptyloxypropionate

4-(5-Pentyloxypyrimidin-(2)-yl)phenyl α-heptyloxypropionate

4-(5-Hexyloxypyrimidin-(2)-yl)phenyl α-heptyloxypropionate

4-(5-Heptyloxypyrimidin-(2)-yl)phenyl α-heptyloxypropionate

4-(5-Octyloxypyrimidin-(2)-yl)phenyl α-heptyloxypropionate

4-(5-Nonyloxypyrimidin-(2)-yl)phenyl α-heptyloxypropionate

4-(5-Propylpyrimidin-(2)-yl)phenyl α-octyloxypropionate

4-(5-Butylpyrimidin-(2)-yl)phenyl α-octyloxypropionate

4-(5-Pentylpyrimidin-(2)-yl)phenyl α-octyloxypropionate

4-(5-Hexylpyrimidin-(2)-yl)phenyl α-octyloxypropionate

4-(5-Heptylpyrimidin-(2)-yl)phenyl α-octyloxypropionate

4-(5-Octylpyrimidin-(2)-yl)phenyl α-octyloxypropionate

4-(5-Nonylpyrimidin-(2)-yl)phenyl α-octyloxypropionate

4-(5-Propyloxypyrimidin-(2)-yl)phenyl α-octyloxypropionate

4-(5-Butyloxypyrimidin-(2)-yl)phenyl α-octyloxypropionate

4-(5-Pentyloxypyrimidin-(2)-yl)phenyl α-octyloxypropionate

4-(5-Hexyloxypyrimidin-(2)-yl)phenyl α-octyloxypropionate

4-(5-Heptyloxypyrimidin-(2)-yl)phenyl α-octyloxypropionate

4-(5-Octyloxypyrimidin-(2)-yl)phenyl α-octyloxypropionate

4-(5-Nonyloxypyrimidin-(2)-yl)phenyl α-octyloxypropionate

4-(5-Propylpyrimidin-(2)-yl)phenyl α-hexyloxypropionate

4-(5-Butylpyrimidin-(2)-yl)phenyl α-hexyloxypropionate

4-(5-Pentylpyrimidin-(2)-yl)phenyl α-hexyloxypropionate

4-(5-Hexylpyrimidin-(2)-yl)phenyl α-hexyloxypropionate

4-(5-Heptylpyrimidin-(2)-yl)phenyl α-hexyloxypropionate

4-(5-Octylpyrimidin-(2)-yl)phenyl α-hexyloxypropionate

4-(5-Nonylpyrimidin-(2)-yl)phenyl α-hexyloxypropionate

4-(5-Propyloxypyrimidin-(2)-yl)phenyl α-hexyloxypropionate

4-(5-Butyloxypyrimidin-(2)-yl)phenyl α-hexyloxypropionate

4-(5-Pentyloxypyrimidin-(2)-yl)phenyl α-hexyloxypropionate

4-(5-Hexyloxypyrimidin-(2)-yl)phenyl α-hexyloxypropionate

4-(5-Heptyloxypyrimidin-(2)-yl)phenyl α-hexyloxypropionate

4-(5-Octyloxypyrimidin-(2)-yl)phenyl α-hexyloxypropionate

4-(5-Nonyloxypyrimidin-(2)-yl)phenyl α-hexyloxypropionate

4-(5-Propylpyrimidin-(2)-yl)phenyl α-pentyloxypropionate

4-(5-Butylpyrimidin-(2)-yl)phenyl α-pentyloxypropionate

4-(5-Pentylpyrimidin-(2)-yl)phenyl α-pentyloxypropionate

4-(5-Hexylpyrimidin-(2)-yl)phenyl α-pentyloxypropionate

4-(5-Heptylpyrimidin-(2)-yl)phenyl α-pentyloxypropionate

4-(5-Octylpyrimidin-(2)-yl)phenyl α-pentyloxypropionate

4-(5-Nonylpyrimidin-(2)-yl)phenyl α-pentyloxypropionate

4-(5-Propyloxypyrimidin-(2)-yl)phenyl α-pentyloxypropionate

4-(5-Butyloxypyrimidin-(2)-yl)phenyl α-pentyloxypropionate

4-(5-Pentyloxypyrimidin-(2)-yl)phenyl α-pentyloxypropionate

4-(5-Hexyloxypyrimidin-(2)-yl)phenyl α-pentyloxypropionate

4-(5-Heptyloxypyrimidin-(2)-yl)phenyl α-pentyloxypropionate

4-(5-Octyloxypyrimidin-(2)-yl)phenyl α-pentyloxypropionate

4-(5-Nonyloxypyrimidin-(2)-yl)phenyl α-pentyloxypropionate

4-(5-Propylpyrimidin-(2)-yl)phenyl α-butyloxypropionate

4-(5-Butylpyrimidin-(2)-yl)phenyl α-butyloxypropionate

4-(5-Pentylpyrimidin-(2)-yl)phenyl α-butyloxypropionate

4-(5-Hexylpyrimidin-(2)-yl)phenyl α-butyloxypropionate

4-(5-Heptylpyrimidin-(2)-yl)phenyl α-butyloxypropionate

4-(5-Octylpyrimidin-(2)-yl)phenyl α-butyloxypropionate

4-(5-Nonylpyrimidin-(2)-yl)phenyl α-butyloxypropionate

4-(5-Propyloxypyrimidin-(2)-yl)phenyl α-butyloxypropionate

4-(5-Butyloxypyrimidin-(2)-yl)phenyl α-butyloxypropionate

4-(5-Pentyloxypyrimidin-(2)-yl)phenyl α-butyloxypropionate

4-(5-Hexyloxypyrimidin-(2)-yl)phenyl α-butyloxypropionate

4-(5-Heptyloxypyrimidin-(2)-yl)phenyl α-butyloxypropionate

4-(5-Octyloxypyrimidin-(2)-yl)phenyl α-butyloxypropionate

4-(5-Nonyloxypyrimidin-(2)-yl)phenyl α-butyloxypropionate

4-(5-Propylpyrimidin-(2)-yl)phenyl α-propyloxypropionate

4-(5-Butylpyrimidin-(2)-yl)phenyl α-propyloxypropionate

4-(5-Pentylpyrimidin-(2)-yl)phenyl α-propyloxypropionate

4-(5-Hexylpyrimidin-(2)-yl)phenyl α-propyloxypropionate

4-(5-Heptylpyrimidin-(2)-yl)phenyl α-propyloxypropionate

4-(5-Octylpyrimidin-(2)-yl)phenyl α-propyloxypropionate

4-(5-Nonylpyrimidin-(2)-yl)phenyl α-propyloxypropionate

4-(5-Propyloxypyrimidin-(2)-yl)phenyl α-propyloxypropionate

4-(5-Butyloxypyrimidin-(2)-yl)phenyl α-propyloxypropionate

4-(5-Pentyloxypyrimidin-(2)-yl)phenyl α-propyloxypropionate

4-(5-Hexyloxypyrimidin-(2)-yl)phenyl α-propyloxypropionate

4-(5-Heptyloxypyrimidin-(2)-yl)phenyl α-propyloxypropionate

4-(5-Octyloxypyrimidin-(2)-yl)phenyl α-propyloxypropionate

4-(5-Nonyloxypyrimidin-(2)-yl)phenyl α-propyloxypropionate

4-(5-Propylpyrimidin-(2)-yl)phenyl α-ethyloxypropionate

4-(5-Butylpyrimidin-(2)-yl)phenyl α-ethyloxypropionate

4-(5-Pentylpyrimidin-(2)-yl)phenyl α-ethyloxypropionate

4-(5-Hexylpyrimidin-(2)-yl)phenyl α-ethyloxypropionate

4-(5-Heptylpyrimidin-(2)-yl)phenyl α-ethyloxypropionate

4-(5-Octylpyrimidin-(2)-yl)phenyl α-ethyloxypropionate

4-(5-Nonylpyrimidin-(2)-yl)phenyl α-ethyloxypropionate

4-(5-Propyloxypyrimidin-(2)-yl)phenyl α-ethyloxypropionate

4-(5-Butyloxypyrimidin-(2)-yl)phenyl α-ethyloxypropionate

4-(5-Pentyloxypyrimidin-(2)-yl)phenyl α-ethyloxypropionate

4-(5-Hexyloxypyrimidin-(2)-yl)phenyl α-ethyloxypropionate

4-(5-Heptyloxypyrimidin-(2)-yl)phenyl α-ethyloxypropionate

4-(5-Octyloxypyrimidin-(2)-yl)phenyl α-ethyloxypropionate

4-(5-Nonyloxypyrimidin-(2)-yl)phenyl α-ethyloxypropionate

4-(5-Propylpyrimidin-(2)-yl)phenyl α-methyloxypropionate

4-(5-Butylpyrimidin-(2)-yl)phenyl α-methyloxypropionate

4-(5-Pentylpyrimidin-(2)-yl)phenyl α-methyloxypropionate

4-(5-Hexylpyrimidin-(2)-yl)phenyl α-methyloxypropionate

4-(5-Heptylpyrimidin-(2)-yl)phenyl α-methyloxypropionate

4-(5-Octylpyrimidin-(2)-yl)phenyl α-methyloxypropionate

4-(5-Nonylpyrimidin-(2)-yl)phenyl α-methyloxypropionate

4-(5-Propyloxypyrimidin-(2)-yl)phenyl α-methyloxypropionate

4-(5-Butyloxypyrimidin-(2)-yl)phenyl α-methyloxypropionate

4-(5-Pentyloxypyrimidin-(2)-yl)phenyl α-methyloxypropionate

4-(5-Hexyloxypyrimidin-(2)-yl)phenyl α-methyloxypropionate

4-(5-Heptyloxypyrimidin-(2)-yl)phenyl α-methyloxypropionate

4-(5-Octyloxypyrimidin-(2)-yl)phenyl α-methyloxypropionate

4-(5-Nonyloxypyrimidin-(2)-yl)phenyl α-methyloxypropionate.

EXAMPLE 15

0.01 mol of 1-{[4-(5-heptylpyrimidin-(2)-yl)phenyl-(1)]-ethylenyl-(2)}4-octyl-(2)-benzoate (α_(D) ²⁰ : +39.0°, c=2 in CH₂ Cl₂) is hydrogenatedin 50 ml of tetrahydrofuran with 2 g of 5% Pd on carbon at roomtemperature under normal pressure until the calculated amount ofhydrogen is taken up. After filtration, evaporation andrecrystallization, 1-{[4-(5-heptylpyrimidin-(2)-yl)phenyl-(1)]ethyl-(2)}4-octyl-(2)-benzoate is obtained, m.p. 44.5°, α_(D) ²⁰ =18.9°, S_(A) /I71°.

The following are prepared in an analogous manner:

1-{[4-(5-Propylpyrimidin-(2)-yl)phenyl-(1)]ethyl-(2)}4-octyl-(2)-benzoate

1-{[4-(5-Butylpyrimidin-(2)-yl)phenyl-(1)]ethyl-(2)}4-octyl-(2)-benzoate

1-{[4-(5-Pentylpyrimidin-(2)-yl)phenyl-(1)]ethyl-(2)}4-octyl-(2)-benzoate

1-{[4-(5-Hexylpyrimidin-(2)-yl)phenyl-(1)]ethyl-(2)}4-octyl-(2)-benzoate

1-{[4-(5-Octylpyrimidin-(2)-yl)phenyl-(1)]ethyl-(2)}4-octyl-(2)-benzoate

1-{[4-(5-Nonylpyrimidin-(2)-yl)phenyl-(1)]ethyl-(2)}4-octyl-(2)-benzoate

1-{[4-(5-Propyloxypyrimidin-(2)-yl)phenyl-(1)]ethyl-(2)}4-octyl-(2)-benzoate

1-{[4-(5-Butyloxypyrimidin-(2)-yl)phenyl-(1)]ethyl-(2)}4-octyl-(2)-benzoate

1-{[4-(5-Pentyloxypyrimidin-(2)-yl)phenyl-(1)]ethyl-(2)}4-octyl-(2)-benzoate

1-{[4-(5-Hexyloxypyrimidin-(2)-yl)phenyl-(1)]ethyl-(2)}4-octyl-(2)-benzoate

1-{[4-(5-Heptyloxypyrimidin-(2)-yl)phenyl-(1)]ethyl-(2)}4-octyl-(2)-benzoate

1-{[4-(5-Octyloxypyrimidin-(2)-yl)phenyl-(1)]ethyl-(2)}4-octyl-(2)-benzoate

1-{[4-(5-Nonyloxypyrimidin-(2)-yl)phenyl-(1)]ethyl-(2)}4-octyl-(2)-benzoate

EXAMPLE 16

0.01 mol of laevorotatory3-[4-(5-heptylpyrimidin-(2)-yl)phenyl-(1)]-2-methylpropionic acid (α_(D)²⁰ =-2.3°), obtained by racemic splitting with (+)-ephedrine andsynthesis of the racemic acid by hydrogenation of the correspondingα-methylcinnamic acid over 5% Pd/carbon in tetrahydrofuran, isesterified with 0.01 mol of 1-hexanol by a method analysis to Example12. After working up and purification, n-hexyl3-[4-(5-heptylpyrimidin-(2)-yl)phenyl-(1)]-2-methylpropionate isobtained.

The following are prepared in an analogous manner:

Hexyl 3-[4-(5-propylpyrimidin-(2)-yl)phenyl-(1)]-2-methylpropionate

Hexyl 3-[4-(5-butylpyrimidin-(2)-yl)phenyl-(1)]-2-methylpropionate

Hexyl 3-[4-(5-pentylpyrimidin-(2)-yl)phenyl-(1)]-2-methylpropionate

Hexyl 3-[4-(5-hexylpyrimidin-(2)-yl)phenyl-(1)]-2-methylpropionate

Hexyl 3-[4-(5-octylpyrimidin-(2)-yl)phenyl-(1)]-2-methylpropionate

Hexyl 3-[4-(5-nonylpyrimidin-(2)-yl)phenyl-(1)]-2-methylpropionate

Hexyl 3-[4-(5-propyloxypyrimidin-(2)-yl)phenyl-(1)]-2-methylpropionate

Hexyl 3-[4-(5-butloxypyrimidin-(2)-yl)phenyl-(1)]-2-methylpropionate

Hexyl 3-[4-(5-pentyloxypyrimidin-(2)-yl)phenyl-(1)]-2-methylpropionate

Hexyl 3-[4-(5-hexyloxypyrimidin-(2)-yl)phenyl-(1)]-2-methylpropionate

Hexyl 3-[4-(5-heptyloxypyrimidin-(2)-yl)phenyl-(1)]-2-methylpropionate

Hexyl 3-[4-(5-octyloxypyrimidin-(2)-yl)phenyl-(1)]-2-methylpropionate

Hexyl 3-[4-(5-nonyloxypyrimidin-(2)-yl)phenyl-(1)]-2-methylpropionate

2-Methylbutyl 3-[4-(5-nonylpyrimidin-(2)-phenyl-(1)]-2-methylpropionate

2-Methylbutyl3-[4-(5-propyloxypyrimidin-(2)-phenyl-(1)]-2-methylpropionate

2-Methylbutyl3-[4-(5-butyloxypyrimidin-(2)-phenyl-(1)]-2-methylpropionate

2-Methylbutyl3-[4-(5-pentyloxypyrimidin-(2)-phenyl-(1)]-2-methylpropionate

2-Methylbutyl3-[4-(5-hexyloxypyrimidin-(2)-phenyl-(1)]-2-methylpropionate

2-Methylbutyl3-[4-(5-heptyloxypyrimidin-(2)-phenyl-(1)]-2-methylpropionate

2-Methylbutyl3-[4-(5-octyloxyoxypyrimidin-(2)-phenyl-(1)]-2-methylpropionate

2-Methylbutyl3-[4-(5-nonyloxyprimidin-(2)-phenyl-(1)]-2-methylpropionate

EXAMPLE 17

0.01 mol of 2-methylbutyl R-p-(5-heptylpyrimidin-2-yl)cinnamate (compareExample 8) are hydrogenated in 50 ml of tetrahydrofuran with 2 g of 5%Pd on carbon at room temperature under normal pressure, until thecalculated amount of hydrogen is taken up. The mixture is then filtered,the filtrate evaporated and the residue recrystallized; 2-methylbutylR-p-(5-heptylpyrimidin-2-yl)-phenylpropionate is obtained, m.p. 16°.

The following are prepared in an analogous manner:

2-Methylbutyl R-p-(5-propylpyrimidin-2-yl)phenylpropionate

2-Methylbutyl R-p-(5-butylpyrimidin-2-yl)phenylpropionate

2-Methylbutyl R-p-(5-pentylpyrimidin-2-yl)phenylpropionate

2-Methylbutyl R-p-(5-hexylpyrimidin-2-yl)phenylpropionate

2-Methylbutyl R-p-(5-octylpyrimidin-2-yl)phenylpropionate

2-Methylbutyl R-p-(5-decylpyrimidin-2-yl)phenylpropionate

2-Octyl R-p-(5-propylpyrimidin-2-yl)phenylpropionate

2-Octyl R-p-(5-butylpyrimidin-2-yl)phenylpropionate

2-Octyl R-p-(5-pentylpyrimidin-2-yl)phenylpropionate

2-Octyl R-p-(5-hexylpyrimidin-2-yl)phenylpropionate

2-Octyl R-p-(5-heptylpyrimidin-2-yl)phenylpropionate

2-Octyl R-p-(5-octylpyrimidin-2-yl)phenylpropionate

2-Octyl R-p-(5-decylpyrimidin-2-yl)phenylpropionate

EXAMPLE 18

7.9 ml of diethyl azodicarboxylate are added at room temperature to asolution of 0.05 mol of 2-(4-hydroxyphenyl)-5-nonylpyrimidine, 5.8 ml ofethyl (s)-lactate and 3.1 g of triphenylphosphine in 150 ml oftetrahydrofuran. The mixture is stirred overnight and evaporated. Theresidue is taken up in 30 ml of 90% methanol and 50 ml of methylenechloride, and 5 ml of H₂ O₂ are added. After 15 minutes, hydrated Na₂ S₂O₅ is added, followed by 100 ml of water. The organic phase is washedand dried.

After evaporation and chromatography on silica gel, optically activeethyl 2-[p-(5-nonylpyrimidin-2-yl)phenoxypropanoate is obtained.

The following are prepared in an analogous manner:

Ethyl 2-[p-(5-propylpyrimidin-2-yl)phenoxy]-propanoate

Ethyl 2-[p-(5-butylpyrimidin-2-yl)phenoxy]-propanoate

Ethyl 2-[p-(5-pentylpyrimidin-2-yl)phenoxy]-propanoate

Ethyl 2-[p-(5-hexylpyrimidin-2-yl)phenoxy]-propanoate

Ethyl 2-[p-(5-heptylpyrimidin-2-yl)phenoxy]-propanoate

Ethyl 2-[p-(5-octylpyrimidin-2-yl)phenoxy]-propanoate

Ethyl 2-[p-(5-propyloxypyrimidin-2-yl)phenoxy]-propanoate

Ethyl 2-[p-(5-butyloxypyrimidin-2-yl)phenoxy]-propanoate

Ethyl 2-[p-(5-pentyloxypyrimidin-2-yl)phenoxy]-propanoate

Ethyl 2-[p-(5-hexyloxypyrimidin-2-yl)phenoxy]-propanoate

Ethyl 2-[p-(5-heptyloxypyrimidin-2-yl)phenoxy]-propanoate

Ethyl 2-[p-(5-octyloxypyrimidin-2-yl)phenoxy]-propanoate

Ethyl 2-[p-(5-nonyloxypyrimidin-2-yl)phenoxy]-propanoate

EXAMPLE 19

Etherification of 2-(4-hydroxyphenyl)-5-nonylpyrimidine with 2-octylbromide in dimethylformamide in the presence of potassium carbonategives 2-[4-(2-octyloxy)phenyl]-5-nonylpyrimidine.

The following are prepared in an analogous manner:

2-[4-(2-Octyloxy)phenyl]-5-propylpyrimidine

2-[4-(2-Octyloxy)phenyl]-5-butylpyrimidine

2-[4-(2-Octyloxy)phenyl]-5-pentylpyrimidine

2-[4-(2-Octyloxy)phenyl]-5-hexylpyrimidine

2-[4-(2-Octyloxy)phenyl]-5-heptylpyrimidine

2-[4-(2-Octyloxy)phenyl]-5-octylpyrimidine

2-[4-(2-Octyloxy)phenyl]-5-propyloxypyrimidine

2-[4-(2-Octyloxy)phenyl]-5-butyloxypyrimidine

2-[4-(2-Octyloxy)phenyl]-5-pentyloxypyrimidine

2-[4-(2-Octyloxy)phenyl]-5-hexyloxypyrimidine

2-[4-(2-Octyloxy)phenyl]-5-heptyloxypyrimidine

2-[4-(2-Octyloxy)phenyl]-5-octyloxypyrimidine

2-[4-(2-Octyloxy)phenyl]-5-nonyloxypyrimidine

2-[4-(2-Methylbutyloxy)phenyl]-5-propylpyrimidine

2-[4-(2-Methylbutyloxy)phenyl]-5-butylpyrimidine

2-[4-(2-Methylbutyloxy)phenyl]-5-pentylpyrimidine

2-[4-(2-Methylbutyloxy)phenyl]-5-hexylpyrimidine

2-[4-(2-Methylbutyloxy)phenyl]-5-heptylpyrimidine

2-[4-(2-Methylbutyloxy)phenyl]-5-octylpyrimidine

2-[4-(2-Methylbutyloxy)phenyl]-5-nonylpyrimidine

2-[4-(2-Methylbutyloxy)phenyl]-5-propyloxypyrimidine

2-[4-(2-Methylbutyloxy)phenyl]-5-butyloxypyrimidine

2-[4-(2-Methylbutyloxy)phenyl]-5-pentyloxypyrimidine

2-[4-(2-Methylbutyloxy)phenyl]-5-hexyloxypyrimidine

2-[4-(2-Methylbutyloxy)phenyl]-5-heptyloxypyrimidine

2-[4-(2-Methylbutyloxy)phenyl]-5-octyloxypyrimidine

2-[4-(2-Methylbutyloxy)phenyl]-5-nonyloxypyrimidine

EXAMPLE 20

A mixture of 11.9 g of 2-p-hydroxyphenyl-5-n-nonylpyrimidine, 10.2 g ofp-(2-methylbutoxy)benzyl bromide (preparable from 4-hydroxybenzaldehydeand 2-methylbutylmesylate in the presence of potassium carbonate in DMF,followed by reduction of the benzaldehyde to benzyl alcohol and reactingit with PBr₃ to give the corresponding benzyl bromide), 8.6 g ofpotassium carbonate and 50 ml of dimethylformamide is heated for 10hours at 90°. The usual working up gives optically active4-(5-n-nonylpyrimidin-2-yl)phenyl p-(2-methylbutoxy)benzyl ether, S-Ch103°, Ch-I 105°.

The following are prepared in an analogous manner:

4-(5-Hexylpyrimidin-2-yl)phenyl p-(2-methylbutoxy)benzyl ether

4-(5-Heptylpyrimidin-2-yl)phenyl p-(2-methylbutoxy)benzyl ether

4-(5-Octylpyrimidin-2-yl)phenyl p-(2-methylbutoxy)benzyl ether

4-(5-Decylpyrimidin-2-yl)phenyl p-(2-methylbutoxy)benzyl ether

4-(5-Pentylpyrimidin-2-yl)phenyl p-(2-methylbutoxy)benzyl ether

4-(5-Butylpyrimidin-2-yl)phenyl p-(2-methylbutoxy)benzyl ether

4-(5-Propylpyrimidin-2-yl)phenyl p-(2-methylbutoxy)benzyl ether

EXAMPLE 21

In an analogous manner to Example 20, 4-(5-n-nonylpyrimidin-2-yl)phenylp-(2-methylbutoxycarbonyl)benzyl ether, m.p. 29°, is obtained from2-p-hydroxyphenyl-5-n-nonylpyrimidine and 2-methylbutylp-bromomethylbenzoate (preparable by azeotropic esterification ofp-bromomethylbenzoic acid with 2-methyl-1-butanol).

The following are prepared in an analogous manner:

4-(5-Hexylpyrimidin-2-yl)phenyl p-(2-methylbutoxycarbonyl)benzyl ether

4-(5-Heptylpyrimidin-2-yl)phenyl p-(2-methylbutoxycarbonyl)benzyl ether

4-(5-Octylpyrimidin-2-yl)phenyl p-(2-methylbutoxycarbonyl)benzyl ether

4-(5-Decylpyrimidin-2-yl)phenyl p-(2-methylbutoxycarbonyl)benzyl ether

4-(5-Pentylpyrimidin-2-yl)phenyl p-(2-methylbutoxycarbonyl)benzyl ether

4-(5-Butylpyrimidin-2-yl)phenyl p-(2-methylbutoxycarbonyl)benzyl ether

4-(5-Propylpyrimidin-2-yl)phenyl p-(2-methylbutoxycarbonyl)benzyl ether

4-(5-Propylpyrimidin-2-yl)phenyl p-(2-octyloxycarbonyl)benzyl ether

4-(5-Butylpyrimidin-2-yl)phenyl p-(2-octyloxycarbonyl)benzyl ether

4-(5-Pentylpyrimidin-2-yl)phenyl p-(2-octyloxycarbonyl)benzyl ether

4-(5-Hexylpyrimidin-2-yl)phenyl p-(2-octyloxycarbonyl)benzyl ether

4-(5-Heptylpyrimidin-2-yl)phenyl p-(2-octyloxycarbonyl)benzyl ether

4-(5-Octylpyrimidin-2-yl)phenyl p-(2-octyloxycarbonyl)benzyl ether

4-(5-Nonylpyrimidin-2-yl)phenyl p-(2-octyloxycarbonyl)benzyl ether

4-(5-Decylpyrimidin-2-yl)phenyl p-(2-octyloxycarbonyl)benzyl ether

EXAMPLE 22

0.04 mol of 5-heptyl-2-(4-styryl)pyrimidine, prepared by methods knownper se, and 0.04 mol of 2-octyl 4-bromobenzoate, prepared from4-bromobenzoic acid and d-2-octanol, are heated under reflux with 0.08mol of triethylamine, 0.1 g of palladium(II) acetate and 0.24 g ofo-tolylphosphine in 50 ml of acetonitrile for 24 hours. Afterevaporation, chromatography on silica gel and recrystallization,oct-2-yl 4-{1-[4-(5-heptylpyrimidin-2-yl)phenyl]ethylenyl-(2)} benzoateis obtained, α_(D) ²⁰ =39.0°.

The following are prepared in an analogous manner:

Oct-2-yl 4-{1-[4-(5-propylpyrimidin-2-yl)-phenyl]-ethylen-2-yl}-benzoate

Oct-2-yl 4-{1-[4-(5-propylpyrimidin-2-yl)-phenyl]-ethylen-2-yl}-benzoate

Oct-2-yl 4-{1-[4-(5-propylpyrimidin-2-yl)-phenyl]-ethylen-2-yl}-benzoate

Oct-2-yl 4-{1-[4-(5-propylpyrimidin-2-yl)-phenyl]-ethylen-2-yl}-benzoate

Oct-2-yl 4-{1-[4-(5-propylpyrimidin-2-yl)-phenyl]-ethylen-2-yl}-benzoate

Oct-2-yl 4-{1-[4-(5-propylpyrimidin-2-yl)-phenyl]-ethylen-2-yl}-benzoate

Oct-2-yl4-{1-[4-(5-propyloxypyrimidin-2-yl)-phenyl]-ethylen-2-yl}-benzoate

Oct-2-yl 4-{1-[4-(5-propylpyrimidin-2-yl)-phenyl]-ethylen-2-yl}-benzoate

Oct-2-yl 4-{1-[4-(5-propylpyrimidin-2-yl)-phenyl]-ethylen-2-yl}-benzoate

Oct-2-yl 4-{1-[4-(5-propylpyrimidin-2-yl)-phenyl]-ethylen-2-yl}-benzoate

Oct-2-yl 4-{1-[4-(5-propylpyrimidin-2-yl)-phenyl]-ethylen-2-yl}-benzoate

Oct-2-yl 4-{1-[4-(5-propylpyrimidin-2-yl)-phenyl]-ethylen-2-yl}-benzoate

Oct-2-yl 4-{1-[4-(5-propylpyrimidin-2-yl)-phenyl]-ethylen-2-yl}-benzoate

EXAMPLE 23

A mixture of 0.7 g of optically active5-[p-(2-methylbutoxy)phenyl]pyrazin-2-ol, 0.6 g of p-octylbenzoic acidchloride and 5 ml of pyridine is stirred overnight. After the usualworking up, optically active2-p-octylbenzoyloxy-5-(2-methylbutoxy)phenylpyrazine is obtained, m.p.53°, c.p. 134°.

The following are prepared in an analogous manner:

2-p-Propylbenzoyloxy-5-(2-methylbutoxy)phenylpyrazine

2-p-Butylbenzoyloxy-5-(2-methylbutoxy)phenylpyrazine, m.p. 78°, c.p.142°

2-p-Pentylbenzoyloxy-5-(2-methylbutoxy)phenylpyrazine, m.p. 66°, c.p.148°

2-p-Hexylbenzoyloxy-5-(2-methylbutoxy)phenylpyrazine

2-p-Heptylbenzoyloxy-5-(2-methylbutoxy)phenylpyrazine, m.p. 63°, c.p.140°

2-p-Nonylbenzoyloxy-5-(2-methylbutoxy)phenylpyrazine

2-p-Decylbenzoyloxy-5-(2-methylbutoxy)phenylpyrazine, m.p. 68°, c.p.130°

2-p-Undecylbenzoyloxy-5-(2-methylbutoxy)phenylpyrazine

2-p-Dodecylbenzoyloxy-5-(2-methylbutoxy)phenylpyrazine

2-p-Propoxybenzoyloxy-5-(2-methylbutoxy)phenylpyrazine

2-p-Butoxybenzoyloxy-5-(2-methylbutoxy)phenylpyrazine

2-p-Pentoxybenzoyloxy-5-(2-methylbutoxy)phenylpyrazine

2-p-Hexoxybenzoyloxy-5-(2-methylbutoxy)phenylpyrazine

2-p-Heptoxybenzoyloxy-5-(2-methylbutoxy)phenylpyrazine

2-p-Octoxybenzoyloxy-5-(2-methylbutoxy)phenylpyrazine, m.p. 116°, c.p.162°

2-p-Nonoxybenzoyloxy-5-(2-methylbutoxy)phenylpyrazine

2-p-Decoxybenzoyloxy-5-(2-methylbutoxy)phenylpyrazine

2-p-Undecoxybenzoyloxy-5-(2-methylbutoxy)phenylpyrazine, m.p. 104°, c.p.151°

2-p-Dodecoxybenzoyloxy-5-(2-methylbutoxy)phenylpyrazine

2-p-Propionyloxybenzoyloxy-5-(2-methylbutoxy)phenylpyrazine

2-p-Butyryloxybenzoyloxy-5-(2-methylbutoxy)phenylpyrazine

2-p-Hexanoyloxybenzoyloxy-5-(2-methylbutoxy)phenylpyrazine

2-p-Octanoyloxybenzoyloxy-5-(2-methylbutoxy)phenylpyrazine

2-p-Nonanoyloxybenzoyloxy-5-(2-methylbutoxy)phenylpyrazine

2-p-Decanoyloxybenzoyloxy-5-(2-methylbutoxy)phenylpyrazine

2-p-Butoxycarbonyloxybenzoyloxy-5-(2-methylbutoxy)phenylpyrazine

2-p-Pentoxycarbonyloxybenzoyloxy-5-(2-methylbutoxy)phenylpyrazine

2-p-Hexoxycarbonyloxybenzoyloxy-5-(2-methylbutoxy)phenylpyrazine

2-p-Octoxycarbonyloxybenzoyloxy-5-(2-methylbutoxy)phenylpyrazine

2-p-Nonoxycarbonyloxybenzoyloxy-5-(2-methylbutoxy)phenylpyrazine

2-p-Decoxycarbonyloxybenzoyloxy-5-(2-methylbutoxy)phenylpyrazine

2-p-Propoxy-5-(2-methylbutoxy)phenylpyrazine

2-p-Butoxy-5-(2-methylbutoxy)phenylpyrazine

2-p-Pentoxy-5-(2-methylbutoxy)phenylpyrazine

2-p-Hexoxy-5-(2-methylbutoxy)phenylpyrazine

2-p-Heptoxy-5-(2-methylbutoxy)phenylpyrazine

2-p-Nonoxy-5-(2-methylbutoxy)phenylpyrazine

2-p-Decoxy-5-(2-methylbutoxy)phenylpyrazine

2-p-Propionyloxy-5-(2-methylbutoxy)phenylpyrazine

2-p-Butyryloxy-5-(2-methylbutoxy)phenylpyrazine

2-p-Pentanoyloxy-5-(2-methylbutoxy)phenylpyrazine

2-p-Hexanoyloxy-5-(2-methylbutoxy)phenylpyrazine

2-p-Heptanoyloxy-5-(2-methylbutoxy)phenylpyrazine

2-p-Octanoyloxy-5-(2-methylbutoxy)phenylpyrazine

2-p-Nonanoyloxy-5-(2-methylbutoxy)phenylpyrazine

2-p-Decanoyloxy-5-(2-methylbutoxy)phenylpyrazine

2-p-Butoxycarbonyloxy-5-(2-methylbutoxy)phenylpyrazine

2-p-Pentoxycarbonyloxy-5-(2-methylbutoxy)phenylpyrazine

2-p-Hexoxycarbonyloxy-5-(2-methylbutoxy)phenylpyrazine

2-p-Heptoxycarbonyloxy-5-(2-methylbutoxy)phenylpyrazine

2-p-Octoxycarbonyloxy-5-(2-methylbutoxy)phenylpyrazine, c.p. 42°

2-p-Nonoxycarbonyloxy-5-(2-methylbutoxy)phenylpyrazine

2-p-Decoxycarbonyloxy-5-(2-methylbutoxy)phenylpyrazine

EXAMPLE 24

A mixture of 6.3 g of S-2-methylbutanol and 50 ml of benzene is treatedwith 0.65 g of sodium. 8.1 g of 3-chloro-6-(p-nonylphenyl)pyridazine areadded to the resultant alcoholate solution. After four hours' boilingunder reflux the mixture is worked up as usual. Optically active3-(2-methylbutoxy)-6-(p-nonylphenyl)pyridazine is obtained, m.p. 78°.

The following are prepared in an analogous manner:

3-(2-Methylbutoxy)-6-(p-butylphenyl)pyridazine

3-(2-Methylbutoxy)-6-(p-pentylphenyl)pyridazine, m.p. 94°

3-(2-Methylbutoxy)-6-(p-hexylphenyl)pyridazine

3-(2-Methylbutoxy)-6-(p-heptylphenyl)pyridazine

3-(2-Methylbutoxy)-6-(p-octylphenyl)pyridazine

3-(2-Methylbutoxy)-6-(p-decylphenyl)pyridazine

3-(2-Methylbutoxy)-6-(p-undecylphenyl)pyridazine

3-(2-Methylbutoxy)-6-(p-dodecylphenyl)pyridazine, m.p. 78°

3-(2-Methylbutoxy)-6-(p-butoxyphenyl)pyridazine

3-(2-Methylbutoxy)-6-(p-pentoxyphenyl)pyridazine

3-(2-Methylbutoxy)-6-(p-hexoxyphenyl)pyridazine

3-(2-Methylbutoxy)-6-(p-heptoxyphenyl)pyridazine

3-(2-Methylbutoxy)-6-(p-octoxyphenyl)pyridazine, m.p. 91°

3-(2-Methylbutoxy)-6-(p-nonoxyphenyl)pyridazine

3-(2-Methylbutoxy)-6-(p-decoxyphenyl)pyridazine, m.p. 87°

3-(2-Methylbutoxy)-6-(p-undecoxyphenyl)pyridazine

3-(2-Methylbutoxy)-6-(p-dodecoxyphenyl)pyridazine

3-(2-Octyl)-6-(p-butylphenyl)pyridazine

3-(2-Octyl)-6-(p-pentylphenyl)pyridazine, m.p. 55°

3-(2-Octyl)-6-(p-hexylphenyl)pyridazine

3-(2-Octyl)-6-(p-heptylphenyl)pyridazine

3-(2-Octyl)-6-(p-octylphenyl)pyridazine

3-(2-Octyl)-6-(p-decylphenyl)pyridazine

3-(2-Octyl)-6-(p-undecylphenyl)pyridazine

3-(2-Octyl)-6-(p-dodecylphenyl)pyridazine, m.p. 56°

3-(2-Octyl)-6-(p-butoxyphenyl)pyridazine

3-(2-Octyl)-6-(p-pentoxyphenyl)pyridazine

3-(2-Octyl)-6-(p-hexoxyphenyl)pyridazine

3-(2-Octyl)-6-(p-heptoxyphenyl)pyridazine

3-(2-Octyl)-6-(p-octoxyphenyl)pyridazine, m.p. 85°

3-(2-Octyl)-6-(p-nonoxyphenyl)pyridazine

3-(2-Octyl)-6-(p-decoxyphenyl)pyridazine, m.p. 87°

3-(2-Octyl)-6-(p-undecoxyphenyl)pyridazine

3-(2-Octyl)-6-(p-dodecoxyphenyl)pyridazine

3-(p-2-Methylbutoxyphenyl)-6-butylpyridazine

3-(p-2-Methylbutoxyphenyl)-6-pentylpyridazine

3-(p-2-Methylbutoxyphenyl)-6-hexylpyridazine

3-(p-2-Methylbutoxyphenyl)-6-heptylpyridazine

3-(p-2-Methylbutoxyphenyl)-6-octylpyridazine

3-(p-2-Methylbutoxyphenyl)-6-decylpyridazine

3-(p-2-Methylbutoxyphenyl)-6-undecylpyridazine

3-(p-2-Methylbutoxyphenyl)-6-dodecylpyridazine

3-(p-2-Methylbutoxyphenyl)-6-butoxypyridazine

3-(p-2-Methylbutoxyphenyl)-6-pentoxypyridazine

3-(p-2-Methylbutoxyphenyl)-6-hexoxypyridazine

3-(p-2-Methylbutoxyphenyl)-6-heptoxypyridazine

3-(p-2-Methylbutoxyphenyl)-6-octoxypyridazine

3-(p-2-Methylbutoxyphenyl)-6-nonoxypyridazine

3-(p-2-Methylbutoxyphenyl)-6-decoxypyridazine

3-(p-2-Methylbutoxyphenyl)-6-undecoxypyridazine

3-(p-2-Methylbutoxyphenyl)-6-dodecoxypyridazine

3-(p-2-Octyloxyphenyl)-6-butylpyridazine

3-(p-2-Octyloxyphenyl)-6-pentylpyridazine

3-(p-2-Octyloxyphenyl)-6-hexylpyridazine

3-(p-2-Octyloxyphenyl)-6-heptylpyridazine

3-(p-2-Octyloxyphenyl)-6-octylpyridazine

3-(p-2-Octyloxyphenyl)-6-decylpyridazine

3-(p-2-Octyloxyphenyl)-6-undecylpyridazine

3-(p-2-Octyloxyphenyl)-6-dodecylpyridazine

3-(p-2-Octyloxyphenyl)-6-butoxypyridazine

3-(p-2-Octyloxyphenyl)-6-pentoxypyridazine

3-(p-2-Octyloxyphenyl)-6-hexoxypyridazine

3-(p-2-Octyloxyphenyl)-6-heptoxypyridazine

3-(p-2-Octyloxyphenyl)-6-octoxypyridazine

3-(p-2-Octyloxyphenyl)-6-nonoxypyridazine

3-(p-2-Octyloxyphenyl)-6-decoxypyridazine

3-(p-2-Octyloxyphenyl)-6-undecoxypyridazine

3-(p-2-Octyloxyphenyl)-6-dodecoxypyridazine

EXAMPLE 25

6.5 g of heptylmalonodialdehydetetraethylacetal, 5.1 g of opticallyactive 4-(2-methylbutyl)mercaptobenzamidine hydrochloride and 10 ml ofdimethylformamide are heated to 150° for 12 hours. The reaction mixtureis then taken up in dichloromethane, washed with sodium hydrogencarbonate solution and water until neutral, dried and the solvent isdistilled off. Optically active2-[4-(2-methylbutyl)mercaptophenyl]-5-n-heptylpyrimidine is obtained.

The following are prepared in an analogous manner:

2-[4-(2-Methylbutyl)mercaptophenyl]-5-octylpyrimidine

2-[4-(2-Methylbutyl)mercaptophenyl]-5-nonylpyrimidine

2-[4-(2-Methylbutyl)mercaptophenyl]-5-decylpyrimidine

2-[4-(2-Methylbutyl)mercaptophenyl]-5-undecylpyrimidine

2-[4-(2-Methylbutyl)mercaptophenyl]-5-dodecylpyrimidine

2-[4-(2-Octyl)mercaptophenyl]-5-heptylpyrimidine

2-[4-(2-Octyl)mercaptophenyl]-5-octylpyrimidine

2-[4-(2-Octyl)mercaptophenyl]-5-nonylpyrimidine

2-[4-(2-Octyl)mercaptophenyl]-5-decylpyrimidine

2-[4-(2-Octyl)mercaptophenyl]-5-undecylpyrimidine

2-[4-(2-Octyl)mercaptophenyl]-5-dodecylpyrimidine

2-[4-Dihydrocitronellylmercaptophenyl]-5-heptylpyrimidine

2-[4-Dihydrocitronellylmercaptophenyl]-5-octylpyrimidine

2-[4-Dihydrocitronellylmercaptophenyl]-5-nonylpyrimidine

2-[4-Dihydrocitronellylmercaptophenyl]-5-decylpyrimidine

2-[4-Dihydrocitronellylmercaptophenyl]-5-undecylpyrimidine

2-[4-Dihydrocitronellylmercaptophenyl]-5-dodecylpyrimidine

EXAMPLE 26

A solution of 0.01 mol of optically active4-(2-methylbutoxy)phenyllithium (prepared from4-bromo-(2-methylbutoxy)benzene and lithium) in 30 ml of toluene isadded dropwise, at -20° under nitrogen, to a solution of 0.01 mol of3-pentylpyridine (which is obtainable by coupling pentylmagnesiumbromide and 3-bromopyridine) in 30 ml of toluene. The reaction mixtureis heated to boiling for 4 hours, then cooled and carefully hydrolyzedwith 10 ml of water. The organic phase is washed with water andsaturated NaCl solution, dried over magnesium sulfate and evaporated.The residue is purified chromatographically on a silica gel column withdiisopropyl ether as the mobile phase. Optically active2-p-(2-methylbutoxy)phenyl-5-pentylpyridine is obtained.

The following are prepared in an analogous manner:

2-p-(2-Methylbutoxyphenyl)-5-butylpyridine

2-p-(2-Methylbutoxyphenyl)-5-pentylpyridine

2-p-(2-Methylbutoxyphenyl)-5-hexylpyridine

2-p-(2-Methylbutoxyphenyl)-5-heptylpyridine

2-p-(2-Methylbutoxyphenyl)-5-octylpyridine

2-p-(2-Methylbutoxyphenyl)-5-nonylpyridine

2-p-(2-Methylbutoxyphenyl)-5-decylpyridine

2-p-(2-Methylbutoxyphenyl)-5-undecylpyridine

2-p-(2-Methylbutoxyphenyl)-5-dodecylpyridine

2-p-(2-Methylbutoxyphenyl)-5-heptoxymethylpyridine

2-p-(2-Methylbutoxyphenyl)-5-hexoxyethylpyridine

2-p-(2-Methylbutoxyphenyl)-5-pentoxypropylpyridine

2-p-(3-Methylpentoxyphenyl)-5-butylpyridine

2-p-(3-Methylpentoxyphenyl)-5-pentylpyridine

2-p-(3-Methylpentoxyphenyl)-5-hexylpyridine

2-p-(3-Methylpentoxyphenyl)-5-heptylpyridine

2-p-(3-Methylpentoxyphenyl)-5-octylpyridine

2-p-(3-Methylpentoxyphenyl)-5-nonylpyridine

2-p-(3-Methylpentoxyphenyl)-5-decylpyridine

2-p-(3-Methylpentoxyphenyl)-5-undecylpyridine

2-p-(3-Methylpentoxyphenyl)-5-dodecylpyridine

2-p-(3-Methylpentoxyphenyl)-5-heptoxymethylpyridine

2-p-(3-Methylpentoxyphenyl)-5-hexoxyethylpyridine

2-p-(3-Methylpentoxyphenyl)-5-pentoxypropylpyridine

2-p-(4-Methylhexoxyphenyl)-5-butylpyridine

2-p-(4-Methylhexoxyphenyl)-5-pentylpyridine

2-p-(4-Methylhexoxyphenyl)-5-hexylpyridine

2-p-(4-Methylhexoxyphenyl)-5-heptylpyridine

2-p-(4-Methylhexoxyphenyl)-5-octylpyridine

2-p-(4-Methylhexoxyphenyl)-5-nonylpyridine

2-p-(4-Methylhexoxyphenyl)-5-decylpyridine

2-p-(4-Methylhexoxyphenyl)-5-undecylpyridine

2-p-(4-Methylhexoxyphenyl)-5-dodecylpyridine

2-p-(4-Methylhexoxyphenyl)-5-heptoxymethylpyridine

2-p-(4-Methylhexoxyphenyl)-5-hexoxyethylpyridine

2-p-(4-Methylhexoxyphenyl)-5-pentoxypropylpyridine

2-p-(5-Methylheptoxyphenyl)-5-butylpyridine

2-p-(5-Methylheptoxyphenyl)-5-pentylpyridine

2-p-(5-Methylheptoxyphenyl)-5-hexylpyridine

2-p-(5-Methylheptoxyphenyl)-5-heptylpyridine

2-p-(5-Methylheptoxyphenyl)-5-octylpyridine

2-p-(5-Methylheptoxyphenyl)-5-nonylpyridine

2-p-(5-Methylheptoxyphenyl)-5-decylpyridine

2-p-(5-Methylheptoxyphenyl)-5-undecylpyridine

2-p-(5-Methylheptoxyphenyl)-5-dodecylpyridine

2-p-(5-Methylheptoxyphenyl)-5-heptoxymethylpyridine

2-p-(5-Methylheptoxyphenyl)-5-hexoxymethylpyridine

2-p-(5-Methylheptoxyphenyl)-5-pentoxypropylpyridine

2-p-(6-Methyloctoxyphenyl)-5-butylpyridine

2-p-(6-Methyloctoxyphenyl)-5-pentylpyridine

2-p-(6-Methyloctoxyphenyl)-5-hexylpyridine

2-p-(6-Methyloctoxyphenyl)-5-heptylpyridine

2-p-(6-Methyloctoxyphenyl)-5-octylpyridine

2-p-(6-Methyloctoxyphenyl)-5-nonylpyridine

2-p-(6-Methyloctoxyphenyl)-5-decylpyridine

2-p-(6-Methyloctoxyphenyl)-5-undecylpyridine

2-p-(6-Methyloctoxyphenyl)-5-dodecylpyridine

2-p-(6-Methyloctoxyphenyl)-5-heptoxymethylpyridine

2-p-(6-Methyloctoxyphenyl)-5-hexoxymethylpyridine

2-p-(6-Methyloctoxyphenyl)-5-pentoxypropylpyridine

2-p-(2-Methylbutyryloxyphenyl)-5-butylpyridine

2-p-(2-Methylbutyryloxyphenyl)-5-pentylpyridine

2-p-(2-Methylbutyryloxyphenyl)-5-hexylpyridine

2-p-(2-Methylbutyryloxyphenyl)-5-heptylpyridine

2-p-(2-Methylbutyryloxyphenyl)-5-octylpyridine

2-p-(2-Methylbutyryloxyphenyl)-5-nonylpyridine

2-p-(2-Methylbutyryloxyphenyl)-5-decylpyridine

2-p-(2-Methylbutyryloxyphenyl)-5-undecylpyridine

2-p-(2-Methylbutyryloxyphenyl)-5-dodecylpyridine

2-p-(2-Methylbutyryloxyphenyl)-5-heptoxymethylpyridine

2-p-(2-Methylbutyryloxyphenyl)-5-hexoxyethylpyridine

2-p-(2-Methylbutyryloxyphenyl)-5-pentoxypropylpyridine

2-p-(4-Methylhexanoyloxyphenyl)-5-butylpyridine

2-p-(4-Methylhexanoyloxyphenyl)-5-pentylpyridine

2-p-(4-Methylhexanoyloxyphenyl)-5-hexylpyridine

2-p-(4-Methylhexanoyloxyphenyl)-5-heptylpyridine

2-p-(4-Methylhexanoyloxyphenyl)-5-octylpyridine

2-p-(4-Methylhexanoyloxyphenyl)-5-nonylpyridine

2-p-(4-Methylhexanoyloxyphenyl)-5-decylpyridine

2-p-(4-Methylhexanoyloxyphenyl)-5-undecylpyridine

2-p-(4-Methylhexanoyloxyphenyl)-5-dodecylpyridine

2-p-(4-Methylhexanoyloxyphenyl)-5-heptoxymethylpyridine

2-p-(4-Methylhexanoyloxyphenyl)-5-hexoxyethylpyridine

2-p-(4-Methylhexanoyloxyphenyl)-5-pentoxypropylpyridine

2-p-(6-Methyloctanoyloxyphenyl)-5-butylpyridine

2-p-(6-Methyloctanoyloxyphenyl)-5-pentylpyridine

2-p-(6-Methyloctanoyloxyphenyl)-5-hexylpyridine

2-p-(6-Methyloctanoyloxyphenyl)-5-heptylpyridine

2-p-(6-Methyloctanoyloxyphenyl)-5-octylpyridine

2-p-(6-Methyloctanoyloxyphenyl)-5-nonylpyridine

2-p-(6-Methyloctanoyloxyphenyl)-5-decylpyridine

2-p-(6-Methyloctanoyloxyphenyl)-5-undecylpyridine

2-p-(6-Methyloctanoyloxyphenyl)-5-dodecylpyridine

2-p-(6-Methyloctanoyloxyphenyl)-5-heptoxymethylpyridine

2-p-(6-Methyloctanoyloxyphenyl)-5-hexoxyethylpyridine

2-p-(6-Methyloctanoyloxyphenyl)-5-pentoxypropylpyridine

2-p-(6-Methyloctanoylphenyl)-5-butylpyridine

2-p-(6-Methyloctanoylphenyl)-5-pentylpyridine

2-p-(6-Methyloctanoylphenyl)-5-hexylpyridine

2-p-(6-Methyloctanoylphenyl)-5-heptylpyridine

2-p-(6-Methyloctanoylphenyl)-5-octylpyridine

2-p-(6-Methyloctanoylphenyl)-5-nonylpyridine

2-p-(6-Methyloctanoylphenyl)-5-decylpyridine

2-p-(6-Methyloctanoylphenyl)-5-undecylpyridine

2-p-(6-Methyloctanoylphenyl)-5-dodecylpyridine

2-p-(6-Methyloctanoylphenyl)-5-heptoxymethylpyridine

2-p-(6-Methyloctanoylphenyl)-5-hexoxyethylpyridine

2-p-(6-Methyloctanoylphenyl)-5-pentoxypropylpyridine

2-p-(3-Chloropentoxyphenyl)-5-butylpyridine

2-p-(3-Chloropentoxyphenyl)-5-pentylpyridine

2-p-(3-Chloropentoxyphenyl)-5-hexylpyridine

2-p-(3-Chloropentoxyphenyl)-5-heptylpyridine

2-p-(3-Chloropentoxyphenyl)-5-octylpyridine

2-p-(3-Chloropentoxyphenyl)-5-nonylpyridine

2-p-(3-Chloropentoxyphenyl)-5-decylpyridine

2-p-(3-Chloropentoxyphenyl)-5-undecylpyridine

2-p-(3-Chloropentoxyphenyl)-5-dodecylpyridine

2-p-(3-Chloropentoxyphenyl)-5-heptoxymethylpyridine

2-p-(3-Chloropentoxyphenyl)-5-hexoxyethylpyridine

2-p-(3-Chloropentoxyphenyl)-5-pentoxypropylpyridine

2-p-(3-Cyanopentoxyphenyl)-5-butylpyridine

2-p-(3-Cyanopentoxyphenyl)-5-pentylpyridine

2-p-(3-Cyanopentoxyphenyl)-5-hexylpyridine

2-p-(3-Cyanopentoxyphenyl)-5-heptylpyridine

2-p-(3-Cyanopentoxyphenyl)-5-octylpyridine

2-p-(3-Cyanopentoxyphenyl)-5-nonylpyridine

2-p-(3-Cyanopentoxyphenyl)-5-decylpyridine

2-p-(3-Cyanopentoxyphenyl)-5-undecylpyridine

2-p-(3-Cyanopentoxyphenyl)-5-dodecylpyridine

2-p-(3-Cyanopentoxyphenyl)-5-heptoxymethylpyridine

2-p-(3-Cyanopentoxyphenyl)-5-hexoxyethylpyridine

2-p-(3-Cyanopentoxyphenyl)-5-pentoxypropylpyridine

2-p-(1,6-Dioxa-8-methyldecylphenyl)-5-butylpyridine

2-p-(1,6-Dioxa-8-methyldecylphenyl)-5-pentylpyridine

2-p-(1,6-Dioxa-8-methyldecylphenyl)-5-hexylpyridine

2-p-(1,6-Dioxa-8-methyldecylphenyl)-5-heptylpyridine

2-p-(1,6-Dioxa-8-methyldecylphenyl)-5-octylpyridine

2-p-(1,6-Dioxa-8-methyldecylphenyl)-5-nonylpyridine

2-p-(1,6-Dioxa-8-methyldecylphenyl)-5-decylpyridine

2-p-(1,6-Dioxa-8-methyldecylphenyl)-5-undecylpyridine

2-p-(1,6-Dioxa-8-methyldecylphenyl)-5-dodecylpyridine

2-p-(1,6-Dioxa-8-methyldecylphenyl)-5-heptoxymethylpyridine

2-p-(1,6-Dioxa-8-methyldecylphenyl)-5-hexoxyethylpyridine

2-p-(1,6-Dioxa-8-methyldecylphenyl)-5-pentoxypropylpyridine

2-p-Octyloxyphenyl-5-(2-methyloctyl)pyridine

2-p-Octyloxyphenyl-5-(3-methyloctyl)pyridine

2-p-Octyloxyphenyl-5-(4-methyloctyl)pyridine

2-p-Octyloxyphenyl-5-(5-methyloctyl)pyridine

2-p-Octyloxyphenyl-5-(6-methyloctyl)pyridine

2-p-Octylphenyl-5-(2-methyloctyl)pyridine

2-p-Octylphenyl-5-(3-methyloctyl)pyridine

2-p-Octylphenyl-5-(4-methyloctyl)pyridine

2-p-Octylphenyl-5-(5-methyloctyl)pyridine

2-p-Octylphenyl-5-(6-methyloctyl)pyridine

2-p-(2-Methylbutoxy)phenyl-5-butyloxypyridine

2-p-(2-Methylbutoxy)phenyl-5-pentyloxypyridine

2-p-(2-Methylbutoxy)phenyl-5-hexyloxypyridine

2-p-(2-Methylbutoxy)phenyl-5-heptyloxypyridine

2-p-(2-Methylbutoxy)phenyl-5-octyloxypyridine

2-p-(2-Methylbutoxy)phenyl-5-nonyloxypyridine

2-p-(2-Methylbutoxy)phenyl-5-decyloxypyridine

2-p-(2-Methylbutoxy)phenyl-5-undecyloxypyridine

2-p-(2-Methylbutoxy)phenyl-5-dodecyloxypyridine

2-p-(2-Methylbutoxy)phenyl-5-heptoxymethyloxypyridine

2-p-(2-Methylbutoxy)phenyl-5-hexoxyethyloxypyridine

2-p-(2-Methylbutoxy)phenyl-5-pentoxypropyloxypyridine

2-p-(3-Methylpentoxy)phenyl-5-butyloxypyridine

2-p-(3-Methylpentoxy)phenyl-5-pentyloxypyridine

2-p-(3-Methylpentoxy)phenyl-5-hexyloxypyridine

2-p-(3-Methylpentoxy)phenyl-5-heptyloxypyridine

2-p-(3-Methylpentoxy)phenyl-5-octyloxypyridine

2-p-(3-Methylpentoxy)phenyl-5-nonyloxypyridine

2-p-(3-Methylpentoxy)phenyl-5-decyloxypyridine

2-p-(3-Methylpentoxy)phenyl-5-undecyloxypyridine

2-p-(3-Methylpentoxy)phenyl-5-dodecyloxypyridine

2-p-(3-Methylpentoxy)phenyl-5-heptoxymethyloxypyridine

2-p-(3-Methylpentoxy)phenyl-5-hexoxyethyloxypyridine

2-p-(3-Methylpentoxy)phenyl-5-pentoxypropyloxypyridine

2-p-(6-Methyloctoxy)phenyl-5-butyloxypyridine

2-p-(6-Methyloctoxy)phenyl-5-pentyloxypyridine

2-p-(6-Methyloctoxy)phenyl-5-hexyloxypyridine

2-p-(6-Methyloctoxy)phenyl-5-heptyloxypyridine

2-p-(6-Methyloctoxy)phenyl-5-octyloxypyridine

2-p-(6-Methyloctoxy)phenyl-5-nonyloxypyridine

2-p-(6-Methyloctoxy)phenyl-5-decyloxypyridine

2-p-(6-Methyloctoxy)phenyl-5-undecyloxypyridine

2-p-(6-Methyloctoxy)phenyl-5-dodecyloxypyridine

2-p-(6-Methyloctoxy)phenyl-5-heptoxymethyloxypyridine

2-p-(6-Methyloctoxy)phenyl-5-hexoxyethyloxypyridine

2-p-(6-Methyloctoxy)phenyl-5-pentoxypropyloxypyridine

2-p-(2-Methyloctoxy)phenyl-5-butyloxypyridine

2-p-(2-Methyloctoxy)phenyl-5-pentyloxypyridine

2-p-(2-Methyloctoxy)phenyl-5-hexyloxypyridine

2-p-(2-Methyloctoxy)phenyl-5-heptyloxypyridine

2-p-(2-Methyloctoxy)phenyl-5-octyloxypyridine

2-p-(2-Methyloctoxy)phenyl-5-nonyloxypyridine

2-p-(2-Methyloctoxy)phenyl-5-decyloxypyridine

2-p-(2-Methyloctoxy)phenyl-5-undecyloxypyridine

2-p-(2-Methyloctoxy)phenyl-5-dodecyloxypyridine

2-p-(2-Methyloctoxy)phenyl-5-heptoxymethyloxypyridine

2-p-(2-Methyloctoxy)phenyl-5-hexoxyethyloxypyridine

2-p-(2-Methyloctoxy)phenyl-5-pentoxypropyloxypyridine

2-p-(2-Methylbutyryloxy)phenyl-5-butyloxypyridine

2-p-(2-Methylbutyryloxy)phenyl-5-pentyloxypyridine

2-p-(2-Methylbutyryloxy)phenyl-5-hexyloxypyridine

2-p-(2-Methylbutyryloxy)phenyl-5-heptyloxypyridine

2-p-(2-Methylbutyryloxy)phenyl-5-octyloxypyridine

2-p-(2-Methylbutyryloxy)phenyl-5-nonyloxypyridine

2-p-(2-Methylbutyryloxy)phenyl-5-decyloxypyridine

2-p-(2-Methylbutyryloxy)phenyl-5-undecyloxypyridine

2-p-(2-Methylbutyryloxy)phenyl-5-dodecyloxypyridine

2-p-(2-Methylbutyryloxy)phenyl-5-heptoxymethyloxypyridine

2-p-(2-Methylbutyryloxy)phenyl-5-hexoxyethyloxypyridine

2-p-(2-Methylbutyryloxy)phenyl-5-pentoxypropyloxypyridine

2-p-(3-Methylpentanoyloxy)phenyl-5-butyloxypyridine

2-p-(3-Methylpentanoyloxy)phenyl-5-pentyloxypyridine

2-p-(3-Methylpentanoyloxy)phenyl-5-hexyloxypyridine

2-p-(3-Methylpentanoyloxy)phenyl-5-heptyloxypyridine

2-p-(3-Methylpentanoyloxy)phenyl-5-octyloxypyridine

2-p-(3-Methylpentanoyloxy)phenyl-5-nonyloxypyridine

2-p-(3-Methylpentanoyloxy)phenyl-5-decyloxypyridine

2-p-(3-Methylpentanoyloxy)phenyl-5-undecyloxypyridine

2-p-(3-Methylpentanoyloxy)phenyl-5-dodecyloxypyridine

2-p-(3-Methylpentanoyloxy)phenyl-5-heptoxymethyloxypyridine

2-p-(3-Methylpentanoyloxy)phenyl-5-hexoxyethyloxypyridine

2-p-(3-Methylpentanoyloxy)phenyl-5-pentoxypropyloxypyridine

2-p-(4-Methylhexanoyloxy)phenyl-5-butyloxypyridine

2-p-(4-Methylhexanoyloxy)phenyl-5-pentyloxypyridine

2-p-(4-Methylhexanoyloxy)phenyl-5-hexyloxypyridine

2-p-(4-Methylhexanoyloxy)phenyl-5-heptyloxypyridine

2-p-(4-Methylhexanoyloxy)phenyl-5-octyloxypyridine

2-p-(4-Methylhexanoyloxy)phenyl-5-nonyloxypyridine

2-p-(4-Methylhexanoyloxy)phenyl-5-decyloxypyridine

2-p-(4-Methylhexanoyloxy)phenyl-5-undecyloxypyridine

2-p-(4-Methylhexanoyloxy)phenyl-5-dodecyloxypyridine

2-p-(4-Methylhexanoyloxy)phenyl-5-heptoxymethyloxypyridine

2-p-(4-Methylhexanoyloxy)phenyl-5-hexoxyethyloxypyridine

2-p-(4-Methylhexanoyloxy)phenyl-5-pentoxypropyloxypyridine

2-p-(6-Methyloctanoyloxy)phenyl-5-butyloxypyridine

2-p-(6-Methyloctanoyloxy)phenyl-5-pentyloxypyridine

2-p-(6-Methyloctanoyloxy)phenyl-5-hexyloxypyridine

2-p-(6-Methyloctanoyloxy)phenyl-5-heptyloxypyridine

2-p-(6-Methyloctanoyloxy)phenyl-5-octyloxypyridine

2-p-(6-Methyloctanoyloxy)phenyl-5-nonyloxypyridine

2-p-(6-Methyloctanoyloxy)phenyl-5-decyloxypyridine

2-p-(6-Methyloctanoyloxy)phenyl-5-undecyloxypyridine

2-p-(6-Methyloctanoyloxy)phenyl-5-dodecyloxypyridine

2-p-(6-Methyloctanoyloxy)phenyl-5-heptoxymethyloxypyridine

2-p-(6-Methyloctanoyloxy)phenyl-5-hexoxyethyloxypyridine

2-p-(6-Methyloctanoyloxy)phenyl-5-pentoxypropyloxypyridine

2-p-(6-Methyloctyloxy)phenyl-5-butyloxypyridine

2-p-(6-Methyloctyloxy)phenyl-5-pentyloxypyridine

2-p-(6-Methyloctyloxy)phenyl-5-hexyloxypyridine

2-p-(6-Methyloctyloxy)phenyl-5-heptyloxypyridine

2-p-(6-Methyloctyloxy)phenyl-5-octyloxypyridine

2-p-(6-Methyloctyloxy)phenyl-5-nonyloxypyridine

2-p-(6-Methyloctyloxy)phenyl-5-decyloxypyridine

2-p-(6-Methyloctyloxy)phenyl-5-undecyloxypyridine

2-p-(6-Methyloctyloxy)phenyl-5-dodecyloxypyridine

2-p-(6-Methyloctyloxy)phenyl-5-heptoxymethyloxypyridine

2-p-(6-Methyloctyloxy)phenyl-5-hexoxyethyloxypyridine

2-p-(6-Methyloctyloxy)phenyl-5-pentoxypropyloxypyridine

2-p-Octyloxyphenyl-5-(2-methyloctyloxycarbonyl)-pyridine

2-p-Octyloxyphenyl-5-(3-methyloctyloxycarbonyl)-pyridine

2-p-Octyloxyphenyl-5-(4-methyloctyloxycarbonyl)-pyridine

2-p-Octyloxyphenyl-5-(5-methyloctyloxycarbonyl)-pyridine

2-p-Octyloxyphenyl-5-(6-methyloctyloxycarbonyl)-pyridine

2-p-Dodecyloxyphenyl-5-(2-methyloctyloxycarbonyl)-pyridine

2-p-Undecyloxyphenyl-5-(2-methylbutoxy)-pyridine

2-p-Decyloxyphenyl-5-(2-methylbutoxy)-pyridine

2-p-Nonyloxyphenyl-5-(2-methylbutoxy)-pyridine

2-p-Octyloxyphenyl-5-(2-methylbutoxy)-pyridine

2-p-Heptyloxyphenyl-5-(2-methylbutoxy)-pyridine

2-p-Dodecanoyloxyphenyl-5-(2-methylbutoxy)-pyridine

2-p-Undecanoyloxyphenyl-5-(2-methylbutoxy)-pyridine

2-p-Decanoyloxyphenyl-5-(2-methylbutoxy)-pyridine

2-p-Nonanoyloxyphenyl-5-(2-methylbutoxy)-pyridine

2-p-Octanoyloxyphenyl-5-(2-methylbutoxy)-pyridine

2-p-Heptanoyloxyphenyl-5-(2-methylbutoxy)-pyridine

EXAMPLE 27

A solution of 0.01 mol n-butyllithium (5% in n-pentane) is addeddropwise at 10°-15° C. to a solution of 0.01 mol of3-[4-(R-2-octyloxy)phenyl]pyridine (obtainable by coupling4-(R-2-octyloxy)phenylmagnesium bromide and 3-bromopyridine) in 30 ml oftoluene and mixture is subsequently heated for 4 hours under reflux.After working up and purification by chromatography,2-n-butyl-5-[4-(R-2-octyloxy)phenyl]pyridine is obtained.

The following are obtained in an analogous manner:

2-Pentyl-5-[4-(R-2-octyloxy)phenyl]pyridine

2-Hexyl-5-[4-(R-2-octyloxy)phenyl]pyridine

2-Heptyl-5-[4-(R-2-octyloxy)phenyl]pyridine

2-Octyl-5-[4-(R-2-octyloxy)phenyl]pyridine

2-Nonyl-5-[4-(R-2-octyloxy)phenyl]pyridine

2-Decyl-5-[4-(R-2-octyloxy)phenyl]pyridine

2-Undecyl-5-[4-(R-2-octyloxy)phenyl]pyridine

2-Dodecyl-5-[4-(R-2-octyloxy)phenyl]pyridine

EXAMPLE 28

A liquid crystalline phase consisting of

10% of 2-p-(4-Methylhexyloxy)phenyl-5-heptylpyrimidine,

4% of 2-p-(4-Methylhexyloxy)phenyl-5-decylpyrimidine,

3% of 2-p-(4-Methylhexyloxy)phenyl-5-dodecylpyrimidine,

8% of 2-p-(5-Methylheptyloxy)phenyl-5-nonylpyrimidine,

8% of 2-p-(5-Methylheptyloxy)phenyl-5-undecylpyrimidine,

6% of 2-p-(5-Methylheptyloxy)phenyl-5-dodecylpyrimidine,

6% of 2-p-(6-Methyloctyloxy)phenyl-5-octylpyrimidine,

30% of r-1-Cyano-cis-4-(4'-octyloxybiphenyl-4-yl)-1-octylcyclohexane

15% of r-1-Cyano-cis-4-(4'-octylbiphenyl-4-yl)-1-butylcyclohexane

10% of 4-(5-Hexylpyrimidin-2-yl)phenyl-2-chloropropionate

has c.p. -18° S_(C*) 66° S_(A*) 70° Ch 82° I.

EXAMPLE 29

A liquid crystalline phase consisting of

10% of 2-p-(4-Methylhexyloxy)phenyl-5-heptylpyrimidine,

4% of 2-p-(4-Methylhexyloxy)phenyl-5-decylpyrimidine,

3% of 2-p-(4-Methylhexyloxy)phenyl-5-dodecylpyrimidine,

8% of 2-p-(5-Methylheptyloxy)phenyl-5-nonylpyrimidine,

8% of 2-p-(5-Methylheptyloxy)phenyl-5-undecylpyrimidine,

6% of 2-p-(5-Methylheptyloxy)phenyl-5-dodecylpyrimidine,

6% of 2-p-(6-Methyloctyloxy)phenyl-5-octylpyrimidine,

30% of r-1-Cyano-cis-4-(4'-octyloxybiphenyl-4-yl)-1-octylcyclohexane,

15% of r-1-Cyano-cis-4-(4'-octylbiphenyl-4-yl)-1-butylcyclohexane and

6% of 1-(4'-Pentylbiphenyl-4-yl)-2-(1-cyano-3-methylcyclohexyl)ethaneand

4% of 4-(5-Nonylpyrimidin-2-yl)phenyl-p-(2-octyloxycarbonyl)benzyl ether

has c.p. -15° S_(C*) 60° S_(A*) 66° Ch 80° I.

EXAMPLE 30

A liquid crystalline material consisting of an achiral base mixturecomprising

3.3% of 2-p-Hexyloxyphenyl-5-heptylpyrimidine,

7.7% of 2-p-Hexyloxyphenyl-5-nonylpyrimidine,

3.3% of 2-p-Heptyloxyphenyl-5-heptylpyrimidine,

3.3% of 2-p-Octyloxyphenyl-5-heptylpyrimidine,

3.3% of 2-p-Nonyloxyphenyl-5-heptylpyrimidine,

25.6% of 2-p-Nonyloxyphenyl-5-nonylpyrimidine,

31.2% of r-1-Cyano-cis-4-(4'-octyloxybiphenyl-4-yl)-1-butylcyclohexane,

15.6% of r-1-Cyano-cis-4-(4'-heptylbiphenyl-4-yl)-1-hexylcyclohexane and

10% of optically active ethyl2-[p-Nonylpyrimidin-2-yl)phenoxy)propanoate

has c.p. -5° S_(C*) 63° S_(A*) 64° Ch 89° I and a spontaneouspolarization of 10.4 nC/cm² at 20°.

EXAMPLE 31

A liquid crystalline phase consisting of the achiral base mixture fromExample 30 and 10% of optically active2-p-(2-octyloxy)-phenyl-5-nonylpyrimidine has c.p. -12° S_(C*) 61°S_(A*) 67° Ch 82° I. This material exhibits a particularly favourablelow temperature behaviour.

EXAMPLE 32

A liquid crystalline phase consisting of the achiral base mixture fromExample 30 and 10% of optically active2,5-dimethylhex-4-enyloxyphenyl-5-hexylpyrimidine has c.p. 0°, S_(C*)68° S_(A*) 72° Ch 91° I.

EXAMPLE 33

A liquid crystalline phase consisting of the achiral base mixture fromExample 30 and 10% of optically active 2-methylbutylp-(5-heptylpyrimidin-2-yl)cinnamate has c.p. 5°, S_(C*) 70° S_(A*) 86°Ch 89° I.

EXAMPLE 34

A liquid crystalline phase consisting of the achiral base mixture fromExample 30 and 10% of optically active 2-octylp-(5-heptylpyrimidin-2-yl)cinnamate has c.p. 3°, S_(C*) 64° S_(A*) 83°Ch 91° I and a spontaneous polarization of 3.3 nC/cm² at 20°.

EXAMPLE 35

A liquid crystalline phase consisting of the achiral base mixture fromExample 30 and 10% of optically active 2-methylbutylp-(5-heptylpyrimidin-2-yl)phenylpropionate has c.p. -2°, S_(C*) 70°S_(A*) 79° Ch 93° I.

EXAMPLE 36

A liquid crystalline phase consisting of the achiral base mixture fromExample 30 and 10% of optically active2-p-(3,7-dimethyloctyloxy)phenyl-5-hexylpyrimidine has c.p. 3°, S_(C*)64° S_(A*) 67° Ch 88° I and a spontaneous polarization of 1.2 nC/cm² at20°.

EXAMPLE 37

A liquid crystalline phase consisting of

3% of 2-p-hexyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-heptyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-octyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-nonyloxyphenyl-5-heptylpyrimidine,

7% of 2-p-hexyloxyphenyl-5-nonylpyrimidine,

25% of 2-p-nonyloxyphenyl-5-nonylpyrimidine,

28% of r-1-cyano-cis-4-(4'-octyloxybiphenyl-4-yl)-1-butylcyclohexane,

4% of r-1-cyano-cis-4-(4'-octylbiphenyl-4-yl)-1-butylcyclohexane,

6% ofr-1-cyano-cis-4-(trans-4-pentylcyclohexyl)-1-(trans-4-pentylcyclohexyl)-cyclohexane

10% of optically active1-(4'-pentylbiphenyl-4-yl)-2-(1-cyano-3-methylcyclohexyl) ethane and

8% of optically active 2-p-dodecylphenyl-5-(2-octyloxy) pyridazine

has c.p. -15° S_(C*) 58° S_(A*) 64° Ch 82° I and a spontaneouspolarization of 19 nC/cm².

EXAMPLE 38

A liquid crystalline phase consisting of

3% of 2-p-hexyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-heptyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-octyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-nonyloxyphenyl-5-heptylpyrimidine,

7% of 2-p-hexyloxyphenyl-5-nonylpyrimidine,

23% of 2-p-nonyloxyphenyl-5-nonylpyrimidine,

28% of r-1-cyano-cis-4-(4'-octyloxybiphenyl-4-yl)-1-butylcyclohexane,

14% of r-1-cyano-cis-4-(4'-heptylbiphenyl-4-yl)-1-hexylcyclohexane,

6% ofr-1-cyano-cis-4-(trans-4-pentylcyclohexyl)-1-(trans-4-pentylcyclohexyl)-cyclohexaneand

10% of optically active 2-p-(2-octyloxycarbonylphenyl)-5-nonylpyrimidine

has S_(C*) 68° S_(A) 81° Ch 96 I.

EXAMPLE 39

A liquid crystalline phase consisting of

3% of 2-p-hexyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-heptyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-octyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-nonyloxyphenyl-5-heptylpyrimidine,

7% of 2-p-hexyloxyphenyl-5-nonylpyrimidine,

23% of 2-p-nonyloxyphenyl-5-nonylpyrimidine,

28% of r-1-cyano-cis-4-(4'-octyloxybiphenyl-4-yl)-1-butylcyclohexane,

14% of r-1-cyano-cis-4-(4'-heptylbiphenyl-4-yl)-1-hexylcyclohexane,

6% ofr-1-cyano-cis-4-(trans-4-pentylcyclohexyl)-1-(trans-4-pentylcyclohexyl)-cyclohexaneand

10% of optically active 2-octylp-[p-(5-nonylpyrimidin-2-yl)-phenoxymehtyl]-benzoate

has S_(C*) 72° S_(A*) 83° Ch 93° I and a spontaneous polarization of 5nC/cm².

EXAMPLE 40

A liquid crystalline phase consisting of

3% of 2-p-hexyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-heptyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-octyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-nonyloxyphenyl-5-heptylpyrimidine,

7% of 2-p-hexyloxyphenyl-5-nonylpyrimidine,

23% of 2-p-nonyloxyphenyl-5-nonylpyrimidine,

28% of r-1-cyano-cis-4-(4'-octyloxybiphenyl-4-yl)-1-butylcyclohexane,

14% of r-1-cyano-cis-4-(4'-heptylbiphenyl-4-yl)-1-hexylcyclohexane,

6% ofr-1-cyano-cis-4-(trans-4-pentylcyclohexyl)-1-(trans-4-pentylcyclohexyl)-cyclohexaneand

10% of optically active p-(5-nonylpyrimidin-2-yl)-phenyl3-chloro-4-(2-octyloxy)-benzoate

has S_(C*) 70° Ch 93° I.

EXAMPLE 41

A liquid crystalline phase consisting of

3% of 2-p-hexyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-heptyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-octyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-nonyloxyphenyl-5-heptylpyrimidine,

7% of 2-p-hexyloxyphenyl-5-nonylpyrimidine,

23% of 2-p-nonyloxyphenyl-5-nonylpyrimidine,

28% of r-1-cyano-cis-4-(4'-octyloxybiphenyl-4-yl)-1-butylcyclohexane,

14% of r-1-cyano-cis-4-(4'-heptylbiphenyl-4-yl)-1-hexylcyclohexane,

6% ofr-1-cyano-cis-4-(trans-4-pentylcyclohexyl)-1-(trans-4-pentylcyclohexyl)-cyclohexaneand

10% of optically active2-p-(2-methylbutoxycarbonyl)-phenyl-5-heptylpyrimidine

has S_(C*) 55° S_(A*) 77° Ch 91° I.

EXAMPLE 42

A liquid crystalline phase consisting of

3% of 2-p-hexyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-heptyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-octyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-nonyloxyphenyl-5-heptylpyrimidine,

7% of 2-p-hexyloxyphenyl-5-nonylpyrimidine,

23% of 2-p-nonyloxyphenyl-5-nonylpyrimidine,

28% of r-1-cyano-cis-4-(4'-octyloxybiphenyl-4-yl)-1-butylcyclohexane,

14% of r-1-cyano-cis-4-(4'-heptylbiphenyl-4-yl)-1-hexylcyclohexane,

6% ofr-1-cyano-cis-4-(trans-4-pentylcyclohexyl)-1-(trans-4-pentylcyclohexyl)-cyclohexaneand

10% of optically active 2-methylbutylp-[p-(5-nonylpyrimidin-2-yl)-phenoxymethyl]-benzoate

has S_(C) 78° S_(A*) 84° Ch 90° I and a spontaneous polarization of 4nC/cm².

EXAMPLE 43

A liquid crystalline phase consisting of

3% of 2-p-hexyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-heptyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-octyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-nonyloxyphenyl-5-heptylpyrimidine,

7% of 2-p-hexyloxyphenyl-5-nonylpyrimidine,

23% of 2-p-nonyloxyphenyl-5-nonylpyrimidine,

28% of r-1-cyano-cis-4-(4'-octyloxybiphenyl-4-yl)-1-butylcyclohexane,

14% of r-1-cyano-cis-4-(4'-heptylbiphenyl-4-yl)-1-hexylcyclohexane,

6% ofr-1-cyano-cis-4-(trans-4-pentylcyclohexyl)-1-(trans-4-pentylcyclohexyl)-cyclohexaneand

10% of optically active2-p-(2-octyloxycarbonyl)-phenyl-5-heptylpyrimidine

has S_(C*) 50° S_(A) 78° Ch 86° I.

EXAMPLE 44

A liquid crystalline phase consisting of

3% of 2-p-hexyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-heptyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-octyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-nonyloxyphenyl-5-heptylpyrimidine,

7% of 2-p-hexyloxyphenyl-5-nonylpyrimidine,

23% of 2-p-nonyloxyphenyl-5-nonylpyrimidine,

28% of r-1-cyano-cis-4-(4'-octyloxybiphenyl-4-yl)-1-butylcyclohexane,

14% of r-1-cyano-cis-4-(4'-heptylbiphenyl-4-yl)-1-hexylcyclohexane,

6% ofr-1-cyano-cis-4-(trans-4-pentylcyclohexyl)-1-(trans-4-pentylcyclohexyl)-cyclohexaneand

10% of optically active p-[p-(5-nonylpyrimidin-2-yl)phenoxymethyl]-(2-methylbutoxy)-benzene

has S_(C*) 80° Ch 100° I.

EXAMPLE 45

A liquid crystalline phase consisting of

3% of 2-p-hexyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-heptyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-octyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-nonyloxyphenyl-5-heptylpyrimidine,

7% of 2-p-hexyloxyphenyl-5-nonylpyrimidine,

23% of 2-p-nonyloxyphenyl-5-nonylpyrimidine,

28% of r-1-cyano-cis-4-(4'-octyloxybiphenyl-4-yl)-1-butylcyclohexane,

14% of r-1-cyano-cis-4-(4'-heptylbiphenyl-4-yl)-1-hexylcyclohexane,

6% ofr-1-cyano-cis-4-(trans-4-pentylcyclohexyl)-1-(trans-4-pentylcyclohexyl)-cyclohexaneand

10% of optically active 1-[p-(5-heptylpyrimidin-2-yl)phenyl]-2-p-(2-octyloxycarbonylphenyl)-ethane

has S_(C) 77° S_(A) 80° Ch 89° I.

EXAMPLE 46

A liquid crystalline phase consisting of

3% of 2-p-hexyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-heptyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-octyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-nonyloxyphenyl-5-heptylpyrimidine,

7% of 2-p-hexyloxyphenyl-5-nonylpyrimidine,

23% of 2-p-nonyloxyphenyl-5-nonylpyrimidine,

28% of r-1-cyano-cis-4-(4'-octyloxybiphenyl-4-yl)-1-butylcyclohexane,

14% of r-1-cyano-cis-4-(4'-heptylbiphenyl-4-yl)-1-hexylcyclohexane,

6% ofr-1-cyano-cis-4-(trans-4-pentylcyclohexyl)-1-(trans-4-pentylcyclohexyl)-cyclohexaneand

10% of optically active 1[p-(5-heptylpyrimidin-2-yl)phenyl]-2-p-(2-octyloxycarbonylphenyl)-ethene

has S_(C*) 73° S_(A*) 78° Ch 91° I.

EXAMPLE 47

A liquid crystalline phase consisting of

3% of 2-p-hexyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-heptyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-octyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-nonyloxyphenyl-5-heptylpyrimidine,

7% of 2-p-hexyloxyphenyl-5-nonylpyrimidine,

23% of 2-p-nonyloxyphenyl-5-nonylpyrimidine,

28% of r-1-cyano-cis-4-(4'-octyloxybiphenyl-4-yl)-1-butylcyclohexane,

14% of r-1-cyano-cis-4-(4'-heptylbiphenyl-4-yl)-1-hexylcyclohexane,

6% ofr-1-cyano-cis-4-(trans-4-pentylcyclohexyl)-1-(trans-4-pentylcyclohexyl)-cyclohexaneand

10% of optically active2-p-(2-methylbutylmercaptophenyl)-5-heptylpyrimidine

has S_(C*) 63° S_(A*) 65° Ch 88° I.

All the phases listed in the examples 38 to 47 exhibit K/S_(C*) phasetransitions below room temperature.

EXAMPLE 48

A liquid crystalline phase consisting of

3% of 2-p-hexyloxyphenyl-5-octylpyrimidine,

3% of 2-p-heptyloxyphenyl-5-octylpyrimidine,

3% of 2-p-octyloxyphenyl-5-octylpyrimidine,

3% of 2-p-nonyloxyphenyl-5-octylpyrimidine,

3% of 2-p-hexyloxyphenyl-5-nonylpyrimidine,

23% of 2-p-nonyloxyphenyl-5-nonylpyrimidine,

25% of r-1-cyano-cis-4-(4'-octyloxybiphenyl-4-yl)-1-octylcyclohexane,

13% of r-1-cyano-cis-4-(4'-heptylbiphenyl-4-yl)-1-hexylcyclohexane,

4% ofr-1-cyano-cis-4-(trans-4-pentylcyclohexyl)-1-(trans-4-pentylcyclohexyl)-cyclohexane

10% of optically active1-(4'-pentylbiphenyl-4-yl)-2-(1-cyano-3-methylcyclohexyl)-ethane and

10% of optically active2-p-(2-methylbutoxy)-phenyl-5-octyloxycarbonyloxypyrazine

has K -18° S_(C*) 61° S_(A*) 67° Ch 84° I and a spontaneous polarizationof 22 nC/cm².

EXAMPLE 49

A liquid crystalline phase consisting of

3% of 2-p-hexyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-heptyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-octyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-nonyloxyphenyl-5-heptylpyrimidine,

7% of 2-p-hexyloxyphenyl-5-nonylpyrimidine,

23% of 2-p-nonyloxyphenyl-5-nonylpyrimidine,

32% of r-1-cyano-cis-4-(4'-octyloxybiphenyl-4-yl)-1-octylcyclohexane,

13% of r-1-cyano-cis-4-(4'-heptylbiphenyl-4-yl)-1-hexylcyclohexane,

3% ofr-1-cyano-cis-4-(trans-4-pentylcyclohexyl)-1-(trans-4-pentylcyclohexyl)-cyclohexaneand

10% of optically active ethyl 2-[p-(5-nonylpyrimidin-2-yl)phenoxy]-propanoate

K<-30° S_(C*) 61° S_(A*) 66° Ch 85° I and a spontaneous polarization of9.7 nC/cm².

EXAMPLE 50

A liquid crystalline phase is prepared which consists of

3% of 2-p-hexyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-heptyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-octyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-nonyloxyphenyl-5-heptylpyrimidine,

7% of 2-p-hexyloxyphenyl-5-nonylpyrimidine,

23% of 2-p-nonyloxyphenyl-5-nonylpyrimidine,

32% of r-1-cyano-cis-4-(4'-octyloxybiphenyl-4-yl)-1-octylcyclohexane,

13% of r-1-cyano-cis-4-(4'-heptylbiphenyl-4-yl)-1-hexylcyclohexane,

3% ofr-1-cyano-cis-4-(trans-4-pentylcyclohexyl)-1-(trans-4-pentylcyclohexyl)-cyclohexaneand

10% of optically active 2-p-(5-methylheptyl)-phenyl-5-nonylpyrazine.

EXAMPLE 51

A liquid crystalline phase is prepared which consists of

3% of 2-p-hexyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-heptyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-octyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-nonyloxyphenyl-5-heptylpyrimidine,

7% of 2-p-hexyloxyphenyl-5-nonylpyrimidine,

23% of 2-p-nonyloxyphenyl-5-nonylpyrimidine,

32% of r-1-cyano-cis-4-(4'-octyloxybiphenyl-4-yl)-1-octylcyclohexane,

13% of r-1-cyano-cis-4-(4'-heptylbiphenyl-4-yl)-1-hexylcyclohexane,

3% ofr-1-cyano-cis-4-(trans-4-pentylcyclohexyl)-1-(trans-4-pentylcyclohexyl)-cyclohexaneand

10% of optically active 2-p-(5-methylheptyl)phenyl-5-(1,4-dioxanonyl)-pyrazine.

EXAMPLE 52

A liquid crystalline phase is prepared which consists of

3% of 2-p-hexyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-heptyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-octyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-nonyloxyphenyl-5-heptylpyrimidine,

7% of 2-p-hexyloxyphenyl-5-nonylpyrimidine,

23% of 2-p-nonyloxyphenyl-5-nonylpyrimidine,

32% of r-1-cyano-cis-4-(4'-octyloxybiphenyl-4-yl)-1-octylcyclohexane,

13% of r-1-cyano-cis-4-(4'-heptylbiphenyl-4-yl)-1-hexylcyclohexane,

3% ofr-1-cyano-cis-4-(trans-4-pentylcyclohexyl)-1-(trans-4-pentylcyclohexyl)-cyclohexaneand

10% of optically active ethyl 2-[p-(5-heptyloxypyrazin-2-yl)phenoxy]-propanoate.

EXAMPLE 53

A liquid crystalline phase is prepared which consists of

3% of 2-p-hexyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-heptyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-octyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-nonyloxyphenyl-5-heptylpyrimidine,

7% of 2-p-hexyloxyphenyl-5-nonylpyrimidine,

23% of 2-p-nonyloxyphenyl-5-nonylpyrimidine,

32% of r-1-cyano-cis-4-(4'-octyloxybiphenyl-4-yl)-1-octylcyclohexane,

13% of r-1-cyano-cis-4-(4'-heptylbiphenyl-4-yl)-1-hexylcyclohexane,

3% ofr-1-cyano-cis-4-(trans-4-pentylcyclohexyl)-1-(trans-4-pentylcyclohexyl)-cyclohexaneand

10% of optically active ethyl 2-[p-(5-heptylpyridin-2-yl)phenoxy]-propanoate.

EXAMPLE 54

A liquid crystalline phase was prepared which consisted of

3% of 2-p-hexyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-heptyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-octyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-nonyloxyphenyl-5-heptylpyrimidine,

7% of 2-p-hexyloxyphenyl-5-nonylpyrimidine,

23% of 2-p-nonyloxyphenyl-5-nonylpyrimidine,

32% of r-1-cyano-cis-4-(4'-octyloxybiphenyl-4-yl)-1-octylcyclohexane,

13% of r-1-cyano-cis-4-(4'-heptylbiphenyl-4-yl)-1-hexylcyclohexane,

3% ofr-1-cyano-cis-4-(trans-4-pentylcyclohexyl)-1-(trans-4-pentylcyclohexyl)-cyclohexaneand

10% of optically active butyl 2-[p-(5-nonylpyridin-2-yl)phenoxy]-propanoate.

EXAMPLE 55

A liquid crystalline phase is prepared which consists of

3% of 2-p-hexyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-heptyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-octyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-nonyloxyphenyl-5-heptylpyrimidine,

7% of 2-p-hexyloxyphenyl-5-nonylpyrimidine,

23% of 2-p-nonyloxyphenyl-5-nonylpyrimidine,

32% of r-1-cyano-cis-4-(4'-octyloxybiphenyl-4-yl)-1-octylcyclohexane,

13% of r-1-cyano-cis-4-(4'-heptylbiphenyl-4-yl)-1-hexylcyclohexane,

3% ofr-1-cyano-cis-4-(trans-4-pentylcyclohexyl)-1-(trans-4-pentylcyclohexyl)-cyclohexaneand

10% of optically active ethyl 2-[p-(5-nonylpyridazin-2-yl)phenoxy]-propanoate.

EXAMPLE 56

A liquid crystalline phase is prepared which consists of

3% of 2-p-hexyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-heptyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-octyloxyphenyl-5-heptylpyrimidine,

3% of 2-p-nonyloxyphenyl-5-heptylpyrimidine,

7% of 2-p-hexyloxyphenyl-5-nonylpyrimidine,

23% of 2-p-nonyloxyphenyl-5-nonylpyrimidine,

32% of r-1-cyano-cis-4-(4'-octyloxybiphenyl-4-yl)-1-octylcyclohexane,

13% of r-1-cyano-cis-4-(4'-heptylbiphenyl-4-yl)-1-hexylcyclohexane,

3% ofr-1-cyano-cis-4-(trans-4-pentylcyclohexyl)-1-(trans-4-pentylcyclohexyl)-cyclohexaneand

10% of optically active ethyl 2-[p-(5-nonylpyridin-2-yl)benzoyloxy]-propanoate.

In the mixtures of optically active materials used in examples 37 and48, in each case one additive is intended to produce a right-handedtwist, while the other additive is intended to produce a left-handedtwist.

We claim:
 1. A nitrogen containing heterocycle of the formula I

    R.sup.1 --A.sup.1 --A.sup.2 --R.sup.2

in which one of R¹ and R² is an alkyl group of 1-15 carbon atoms or analkyl group of 1-15 carbon atoms in which one or two nonadjacent CH₂groups are replaced by at least one of --S--, --O--, --CO--, --O--CO--,--CO--O-- or --CH═CH--, and the other radical R¹ or R² is an opticallyactive organic radical with an asymmetric carbon atom having the formula##STR25## wherein X is --O--, Q is --CH₂ CH₂ --, Y is F, R is an alkylgroup of 1 to 10 carbon atoms A¹ is --A--, --A⁴ --Z³ --A-- or --A--Z³--A⁴, A is pyrimidine-2,5-diyl, A² and A⁴ each independently is1,4-cyclohexylene or 1,4-phenylene which is unsubstituted or substitutedby one or two F atoms, and Z³ is --CO--O--, --O--CO--, --OCH₂ --, --CH₂O--, --CH₂ CH₂ -- or a single bond.
 2. A nitrogen-containing heterocycleaccording to claim 5, wherein one of the radicals R¹ and R² is alkyl,--O--, alkyl, oxaalkyl, --COO-alkyl, --OCO-alkyl, --CO-alkyl or alkenyl,and each radical has 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15carbon atoms.
 3. A nitrogen containing heterocycle according to claim 6,wherein one of the radicals R¹ and R² is straight-chain alkyl of 2, 3,4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15 carbon atoms.
 4. A nitrogencontaining heterocycle according to claim 1, wherein A¹ --A² is astructural element of formula 1: ##STR26##
 5. A nitrogen-containingheterocycle according to claim 1, where A² and A⁴ are each1,4-phenylene.
 6. A nitrogen-containing heterocycle of the formula##STR27## in which R¹ is alkyl group of 1-15 carbon atoms, A¹ ispyrimidine-2,5-diylA² is 1,4-phenylene which is substituted by one Fatom, X is --O--, Q is --CH₂ CH₂ -- or --CH₂ --, Y is F, and R is analkyl group of 1 to 10 carbon atoms.
 7. A nitrogen containingheterocycle of the formula I

    R.sup.1 --A.sup.1 --A.sup.2 --R.sup.2

in which R¹ is an alkyl group of 1-15 carbon atoms in which one or twononadjacent CH₂ groups are replaced by at least one of --S--, --CO--,--O--CO--, --CO--O--, or --CH═CH--, and R² is ##STR28## wherein C* is anasymmetric carbon atom X is O Q is --CH₂ -- or a single bond Y is F R isC₁₋₁₀ alkyl and --A¹ --A² -- is ##STR29##
 8. A compound of claim 7wherein X is --O--, Q is --CH₂ -- and R¹ is C₁₋₁₅ alkyl.
 9. A nitrogencontaining heterocycle of the formula I

    R.sup.1 --A.sup.1 --A.sup.2 --R.sup.2

in which R¹ is C₁₋₁₅ alkyl R² is ##STR30## wherein C* is an asymmetriccarbon atom X is O, Q is a single bond Y is F R is C₁₋₁₀ alkyl and --A¹--A² -- is ##STR31##